§ Episode March 4, 2022 21:35 Scott Dillingham

How to Manage Real Estate Investments While Working Full-Time Without Burning Out

March 4, 2022 · Scott Dillingham

Most real estate investors do not quit their jobs before building their portfolio — they build it while working. In this episode, Scott Dillingham shares the systems and delegation strategies that let busy professionals manage a growing real estate portfolio without sacrificing t…

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Most real estate investors do not quit their jobs before building their portfolio — they build it while working. In this episode, Scott Dillingham shares the systems and delegation strategies that let busy professionals manage a growing real estate portfolio without sacrificing their career.

Scott emphasizes building a strong team: Property managers handle tenant issues/vacancies, investor-focused lenders optimize financing/structure for growth, specialized realtors avoid high-turnover areas, knowledgeable bankers accelerate down payments, inspectors/lawyers versed in LTB matters prevent pitfalls—even contractors tested on small jobs first.

He advises automating finances: Direct deposit rents into one account, auto-withdraw mortgages/utilities/taxes (waives setup fees, saves time); set reserves (3 months rent/property) for vacancies; avoid principal paydowns during acquisition to maintain low debt ratios/maximize qualifications.

For experienced investors: Use variable rates initially for flexibility/low penalties, lock fixed later if needed—prioritizes purchasing power over quick payoff.

In 2025, Ontario's investment landscape sees softening prices (~3% drop to $800K avg single-family) amid BoC stability at ~2%, but rising rents (up 5-7%) boost multifamily cash flow despite supply shortages—favoring automated teams in uncertain recovery, per CMHC, RBC, and TD reports.

This episode empowers busy professionals to invest efficiently through teams and automation in Canada's 2025 market.

Guest Bio 
Scott Dillingham is the host of The Wisdom, Lifestyle, Money Show and founder of LendCity Mortgages in Windsor, Ontario, specializing in home and investment financing. As an experienced investor, Scott shares practical strategies for balancing life and portfolios. Passionate about efficiency, he draws from personal lessons. Connect with Scott at lendcity.ca, call 519-960-0370, or listen for investing insights.


Key Takeaways

  • Build Power Team: Include property managers for tenant handling, investor-savvy lenders/bankers for optimized financing/down payments, specialized realtors for low-vacancy areas, LTB-knowledgeable lawyers, and tested contractors—start small to evaluate.
  • Automate Expenses: Direct rents to one account; auto-debit mortgages/utilities/taxes (avoids fees, saves time)—handles bill dates effortlessly for multiple properties.
  • Reserves Essential: Keep 3 months rent/property minimum in accounts for vacancies; automates stability without constant monitoring.
  • Debt Strategy: Avoid extra principal payments during growth—keeps ratios low for more qualifications; use variable rates for flexibility, convert to fixed if rates rise.
  • Time Savings: Automation frees focus for life/family; property managers eliminate daily headaches like repairs/disputes.
  • Beginner Tip: First property toughest (full vacancy coverage)—team mitigates; evolve to multifamily for better flow once comfortable.
  • 2025 Outlook: Softening prices but rising rents (5-7%) enhance cash flow; BoC at ~2% aids affordability—teams/automation key in recovery.

Resources and Links


Call to Action 
If Scott Dillingham's tips on teams and automation for busy investors in 2025's rising-rent market help your portfolio, visit lendcity.ca or call 519-960-0370 for referrals/consultations. Share this episode with time-strapped investors—tag us on social media! What's your automation hack? Leave a review on Apple Podcasts or Spotify to aid others with 2025 trends, team-building strategies, or financial optimization. Tune in next week for more on wealth management.

  • (00:00) - - Real Estate Investing for Busy Professionals: Why Time Management Matters
  • (03:45) - - Avoiding Slumlord Pitfalls: Renovate for Great Tenant Experiences
  • (06:20) - - Building a Power Team: Property Managers, Lenders & Realtors
  • (12:10) - - Vetting Contractors & Team Referrals for Investors
  • (15:30) - - Automating Rental Property Expenses: Rents, Mortgages & Taxes
  • (20:45) - - Utility Automation & Reserve Funds for Vacancy Protection
  • (24:15) - - Variable vs Fixed Mortgages: Boost Purchasing Power
  • (27:50) - - Final Tips: Reinvest for Growth & Save Time Everywhere

Transcript

Introduction

Welcome to the Wisdom Lifestyle Money Show. I'm your host, Scott Dillingham. The show is designed to help Canadians invest better in Canada and the United States. We are the North America-based mortgage financing lender and provide education to both countries.

Discover how you can become a better investor and access the financing you need. Welcome back to the Wisdom Lifestyle Money Show.

I'm your host, Scott Dillingham. Today, I'm gonna dive into a topic that I wish I knew years ago. And it was how to successfully manage a real estate business when you're busy. So I find that is the biggest challenge for people that want to get into investing, especially the ones with good incomes and down payments to make this happen.

Often you're too busy with work, you're too busy with life, you could have family, kids, all the good stuff. What happens is a lot of people that would be investing are not investing. And real estate investing is actually very important. There's lots of people, even friends of mine, that are tenants and they talk about their landlord and how they don't like their landlord and this and that.

The Core Idea

And not every landlord is at the same level as others. But what happens is a landlord purchases a property and a good landlord will renovate it and turn it into an amazing place to live for somebody.

So that's how I run my portfolio. And that's how I suggest everybody does it. But yes, the slumlords, deferred maintenance, not being available, returning calls, that's not good. And that can happen if you're too busy and you try to get into real estate investing.

Again, I want to share with you tips and advice that I wish I knew when I started investing in real estate because it would have made my first few years that much easier. So I've spoken about it in other episodes, but really it's super important to have the right team. Absolutely, I would say you want to have a property manager. So again, I know I covered this in a previous episode, but the thing is with a property manager is they take a lot of the landlord and tenant issues away from you.

So you get to focus on your life and what you want to do and not dealing with broken toilets or tenant disputes or anything like that. So a property manager has a cost, but if you look at it like how much is my time worth? Is me paying this much to the property manager worth that time? And of course it is because time is our most valuable asset.

Deep Dive

It's the only thing we can really not create more of. In our lives.

Time is super important. The first part of this is about your team. So obviously, yes, you want to get your property manager. You want to deal with an excellent mortgage lender like ourselves or any other lender that specializes in rental properties.

I do not recommend just going to a mortgage broker or a bank and applying. They may be able to help you for the first one, two, three, maybe even four. But a lot of times we find we get clients that have all these properties and they're stuck and they can't move forward. So we undo the lending and the structuring that they've set up and we reset it and swap lenders and tweak things.

And we do that to optimize the cash flow of their portfolio, but also to maximize the amount of mortgages they can get. Because if you choose your lenders out of the wrong order, you're going to limit yourself.

Practical Steps

So again, back to the team, right? You've got to have that good mortgage lender or broker or bank that specializes in working with investors. You need to have a good realtor as well. A real estate agent can sell you any property.

But if you're working with one that specializes in working with investors, they're going to say, you know what? You should avoid this area. The vacancy is a little high over here and the turnover is high too, because it's not a great area. So in case you don't know what that means, turnover is if somebody doesn't rent a property for a long period of time and then they leave and then you get a new tenant and they quickly leave, that's a high turnover.

Or if someone wants to stay for a couple of years, that it's a better and stronger property. Oh, a good realtor who understands working with investors, a lot of them, like I said, will sell you a rental property and say, oh yeah, we work with investors. But in Windsor, there's probably less than 10 realtors that I know of that actually really focus on real estate investors. And I might be wrong with that count, but that's just what I know personally.

But there's more than 2000 realtors in Windsor and Essex County. So it's just a fraction of it. So there's a very big chance if you don't know who you're dealing with, you could be dealing with somebody who's not a good fit for you. So again, when it comes to investment properties, it's all about your team.

Key Takeaways

And I would say even your banker, right? So even if you don't get your mortgage from a bank, it's good to work with somebody in the bank that understands money. And I know it's like an oxymoron because you would think people working in the bank understand money, but most of them don't. A lot of them are just there.

It's just a job to get them to where they want to be. It's just something in the middle there. But you want to understand or work with somebody who understands banking because then they can make some tips for you. They can show you how to increase your down payments faster.

There's all kinds of cool stuff that they can show you that most regular bankers are not aware of. Okay. Having a banker is super important. Having a home inspector is super important.

Having a good lawyer who understands investors is important as well because most lawyers will be able to transact your real estate purchase or refinance. But very few know little about the landlord and tenant boards. It's super important to know about that, especially if you're getting into investing. Again, it's all about the team and all these team members.

Resources

If you leverage them and create this team together and collectively, they will save you a lot of time. So I think that's truly one of the first and most important steps is to have that solid team from everyone.

Even contractors. You've got to look at that. Like contractors, there's so many people. Now, if you're looking for any realtor recommendations or referrals, please let me know.

Give my office a call. I don't care if you use us for the mortgage or not. Like we want to help and we'll show you. We'll guide you to who we know that does investment properties.

We will not recommend someone to you that we do not know. And if we don't know someone in your area, we'll also let you know. But we know tons of realtors across Canada.

Introduction

So give us a call. My office lines 519-960-0370. Or you can email us at team.

ca. So that's L-E-N-D-I-T-Y dot C-A. And just say, hey, I'm looking for a referral in this market. And I will let you know as far as the realtors are concerned with who's best.

We do know a lot of lawyers in different markets and a lot of good property managers as well. So we can make those referrals to you as well if that's what you're looking for. We generally do not recommend any type of contractor. Find with COVID, supply issues with materials.

The good contractors that I know and use are they've quit. They're booked for a whole year. It's so hard to get good work right now from a contractor. Not to say it's impossible, but that's an area that I think is tough to make referrals in.

The Core Idea

And we don't recommend any contractors unless we know and see their work because we don't want to suggest someone to you and again, it's the project turns out nasty. So we want to avoid that at all costs. We won't make any contractor recommendations. But so again, back to the team.

So every single person is important and you might not think you need to create a team with that many people in it. And you need to, even if you're not going to use a home inspector on this purchase, because maybe the seller or like just whatever the scenario is and you feel confident about not using a home inspector, you still need to have one on your team because the next property is going to come up where you may not have that confidence. And you're going to be like, you know what?

I need a home inspection on this thing and you will have your contacts. So even if you don't need the person now, today, even in the near future, it's still good to call them up and say, hey, I'm building my power team. I just want to interview you. Just see if we can connect.

And if we do, I'll use you as project to come up and that's it. So you want to create that power team. You want to do it early, right? If you have the right team, you're laughing.

Deep Dive

And my first property was a single family property. I don't know if you heard my beginning story, but the, there was an investor from Toronto. He asked me to find a property, like a wholesale deal. He was going to buy it.

So I found a nice wholesale deal. I put in a cash offer because that's what his instructions were to secure it. I got the property and he ran away.

So I had to do it. Like I had to take over and purchase this and move forward. And again, I'm so glad it happened because I, we had to repair everything in the house and there's not a renovation or a fix that I'm scared to do. But what I did discover is I did have a couple of contractors and what I did is I started them with a small project on the house to test them out and see if I liked their work and working with them, that type of thing.

And I did that until I found one that was really good. And then I had them do the whole, like the rest of the property. So if you're getting into a big project and you don't have a good contractor, I recommend just starting them with just a small job and just see if you can connect, see if they show up in a timely manner, if they're professional, like their work quality. And that's how I would work and find a good contractor.

Practical Steps

Now when we come back, I've talked about the team. I'm going to talk about the finances. So we have to take a quick pause and we'll dive into the finances and how to optimize everything on autopilot.

So it requires none of your time. Welcome back to the show. So this part, I'm excited about because dealing with the team, I think a lot of investors do know that. I like to stress it because again, a lot of new investors, they don't build the correct team.

So I do like to talk about it, but the experienced investors know how important a good team is. So the first part of the topic for any investor who's experienced, you probably want to fast forward through, right? Because it's something you already know. But financial part of things and automating, that's really cool that I see a lot of investors failing at and I did it to my whole portfolio and it is absolutely amazing.

Just the time savings. It's a really simple process. You just want to automate all of the expenses. So with my property manager, he actually has direct deposit.

Key Takeaways

Most of them will have direct deposit for you. I just, I have one bank account and I have him direct deposit all the rent into that bank account. And then what I've done is I've set up all of my mortgages to also withdraw from the same bank account.

So that's all taken care of. Now, property tax is debatable. I get asked all the time, should you include property taxes with your mortgage or should you pay them to the city separately? I like to pay it to the city separately.

I don't like including them in the mortgage. The reason is some years that the city or town that you're investing in, they may or may not increase the taxes. I've had some investment years where they did not increase the taxes. I had some years where they increased them a lot and other years where they increased them a little.

So if you build in your taxes with your mortgage, the lender's going to just take an average. And what happens is at the end of the year, they're going to say, okay, I'll pick an easy number just to go with it. Let's pretend your taxes are $1,000 for the whole year on a property. That's super low, but just as an example.

Resources

And they feel that the market's going crazy and the taxes are going to go up 5% to 10% this year. Then they will make your payments $1,050 to $1,100. So that's what they start collecting from you. However, if the city says, no, we're only going to increase taxes 2% this year, then the bank is collecting more money from you than what they actually pay out in taxes.

And the banks, they like to get a surplus from you as well. They don't like to have to pay tax bills and then you pay them back. They're doing it as a service.

They're not charging for it. So they don't like to use their money. They want to use your money. So they charge you extra to build up that surplus.

So if the taxes go up, they're not paying out of pocket while they wait to collect it from you with the regular installments. Well, just with the way that they do it, you get the money back. If it's the end of the year and there's a big credit, they'll issue you a check. They'll allow you to pay it to your mortgage.

Introduction

There's different options. But I'd rather have my money with me now as opposed to having the bank hold it, me not making anything off of it and then just getting it at the end of the year.

Like, I don't like that. I want my money now. I prefer to pay my taxes direct through the city and not with the mortgage lender.

Now, it's pretty easy. You just call up your city that you're buying in and you just say, hey, I need the pre-authorized debit form to set up my taxes for automatic payments.

And it gets done. So I do the taxes automatically. There's some properties like duplexes that have single meters or even larger units with less meters than there are units. Sometimes there's meters for common areas that's billed to the landlord and the tenants have their own separate meters.

The Core Idea

So they're paying their own utilities. So where possible, I get my tenants to pay their own utilities. However, if there's a shared meter, I will always set up automatic payments. Plus, even if you have a separate meter, what the utility companies do, I can't say they all do, but all the ones that I've personally dealt with is when your tenant moves out and they set up an account for you, they charge you a fee to set up the account.

Where if you have it automatically set up through them where they can take any payments or whatever from your bank account, a lot of times they waive those setup fees between every single tenant. By automating that process, it's been really cool. Plus, I had it at one point where in my online banking, I actually couldn't add any more bill payees because I had so many properties and so many things going on and this account here and that account there, different cities, right? It was so much that I actually couldn't add the bill payee on my online banking to pay the property taxes.

So I had to delete like a credit card or something. I had to delete something to add in the tax bill to pay it.

So it was a huge pain in the butt. Automating it was absolutely incredible. And then obviously any other expenses like home insurance, right? I would automate that from the bank account.

Deep Dive

And when you take all the expenses that are rental property expenses and you withdraw them from the account automatically and you just look at your account, you get an average of how much is left over at the end of paying all your expenses. So I would set a bare minimum of what I need for in like in my bank account. A lot of times the suggestion would be like three months rent per property. That's been my focus of what to have in there as a minimum.

Everyone's different. I didn't want to do much more than that. I've heard some people say you should have six months rent per property. I think that's a little high personally.

If I can have those funds instead and invest them somewhere else, I'd rather do that. And for me, it's worked perfect. So make up your own thing, but I would have a reserve fund in there. So that way if there is vacancies, right, the mortgage payments, because they're coming out, it's automated at this point.

So you want to still make sure you have that reserve fund in case there's some vacancies on a property or multiple properties. So that's all automated and then I send myself the balance and I use it for whatever I want to use it for. And then taxes and I don't do any mortgage principal pay downs while I'm growing my portfolio. And there's a lot of clients and a lot of people I speak to that are as a homeowner, the mindset is pay off the debt, pay off the house as quickly as it can, credit card debt's bad, like all this stuff's bad.

Practical Steps

So you want to pay off debts. When you're an investor, you still, I still don't like owing anything on my credit card and I'll pay it like every single month in full. And if I can't, like it pisses me off. It's very rare that I don't pay it in full.

But when you have those big random expenses come up and I could take money from other accounts and pay it in full, but I try to, if it's for rental properties, I try to only have the rentals pay it. If it's for my business, I try to only have my business paid. I try not to take anything from the other accounts. But long story short, what I'm saying here is you want to know exactly what's coming in, what's going out.

And with investors, you have to understand that the debt is not bad. So you don't want to pay off your mortgage right away if your goal is to acquire additional properties.

That doesn't make sense. Plus, if you increase your mortgage payments on your rentals or even your owner-occupied home while you're acquiring rentals, it will go negatively against your debt-to-income ratio and it makes it harder for you to qualify. So my suggestion to all investors is don't worry about paying off your mortgages now.

Key Takeaways

Use that money. Build up your down payments. Use it to upgrade your properties.

Like, reinvest into your business. Don't pay down the mortgages.

Extra. Now, then what you do is once you've acquired the enough, like, the amount of properties that you're satisfied with, then you start changing your focus and working on paying them down. But while you're building up, you want to keep your debt ratios as low as possible. So another quick tip here, which is not about necessarily automating, but when you are qualifying for the mortgages, I do recommend the variable as well.

I know I spoke about that in another episode, but for investors, absolutely go with the variable because what happens is when you're qualifying for mortgages, it's based on your mortgage payment. And I know variables going up, we all know it, but at least if you're buying something relatively in the short term, like relatively quick, the variable mortgage has a lower payment than the fixed, right? Sometimes, not half, but a lot of times, it's drastically reduced compared to the fixed, but really improves your purchasing power. And then once you've acquired your property, if you're absolutely one of those people that hate the variable and you only want to go with fixed, then you lock in your fixed rate.

Resources

That way you are leading the system, right? You're getting that variable which has lower mortgage payment, which is allowing you to qualify for more. And then when you lock in that fixed rate, only if you're scared of variable, I keep all mine variable, I don't lock them in at all. I don't care what the rates are doing in the market.

The variables, my exit strategy in case I need to upgrade to something bigger and better. So I will never get rid of my variables. I don't care what the rates are doing. But if you are someone that's scared and you want to lock in, you can do that.

But pretty much the point of the second part of the show is to automate all of your expenses and income coming in for the rental property so you don't have to think about it. Once you've one property, it's easy to pay the bills. But once you start getting handfuls, all the bill dates are due at different dates. It can almost be like a full time job paying the bills.

I know it sounds silly, but like it is when you got stuff going on over here and then you're like, did I pay that bill? And it's a lot where if it's all automated, it's completely off of you and it saves me so much time.

Introduction

So we're back to the time thing again. having the right team for your portfolio and automating everything that you can on your end saves you so much time. Just a quick tip and not to promote, but Amazon subscribe and save. I went through everything in my house that I order all the time and I figured out how frequently we bought these items and I set all of that up on subscribe and save, right?

So I'm saving myself time. I'm not going to the store and buying those things and it's coming when we need it and it's just time. So when we go to the grocery store, it's a quick in and out.

It's not this long. Let's go over here.

Let's go over there. Everything saves you time if you can optimize your life. So that would be my message for you today.

The Core Idea

I hope this helped again. If you need to reach out to me, you're looking for a realtor recommendation or property manager or lawyer, give us a call 519-960-0370.

Thanks so much. Have a great day. Thank you so much for tuning into the show today. If you found value, please follow the show and rate it 5 stars.

It would mean the world to me. And lastly, all the resources that we spoke about are at the bottom of the show notes. Looking forward to seeing you in the next episode.

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