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Tips to Start Investing in Rentals Later in Life

Updated: Aug 23, 2021





“The best time to plant a tree was 20 years ago. The second-best time is now.” —Chinese Proverb


Think you missed the boat on real estate investing? That it’s somehow “too late” because you’ve reached your 40s, 50s, 60s, or even 70s?

Think again. Real estate investing is not the exclusive domain of the young, hip, and unattached. In fact, middle-aged and senior investors bring some unique experiences and advantages to the table. Sure, you might have kids. A spouse. A demanding job. So what? You think you’re the first parent who works full-time to buy a rental property?

You probably have a lot more savings than the 23-year-old who’s trying to buy their first property. For that matter, you probably have experience buying real estate—in the form of a home. You’ve been through the mortgage financing process before and know some of the pitfalls to watch out for. Here are a few pointers for older adults, to buy their first rental property in middle age or later.


5 Smart Ways to Start Investing in Rentals Later in Life

1. Leverage (and build!) your network.


Think that 23-year-old rascal has a network like yours? Fuhget about it.

Take advantage of your superior network and double down on building an even stronger one. Who do you know in the real estate industry? In the mortgage industry? In the construction and contracting industries? Who do you know who has more money than they know what to do with and is looking for a project to invest in?

The electrician in your Friday poker group can refer you to trustworthy and affordable general contractors and handymen. The real estate agent in your bridge club may not service the area where you’re looking to invest, but she can refer you to someone who can. Don’t stop at friends of friends. Join local real estate investing Facebook groups. Participate in our local real estate investing forums. Sign up with local wholesalers, turnkey providers, and other off-market sellers in your area. Start assembling your dream team. After all, real estate investing is a team sport, and you have several more decades’ worth of contacts to draw on to fill out your roster!


2. Capitalize on your existing capital.


After being employed for several decades, you should have far more money set aside than some 23-year-old just out of college who’s scraping by on their entry-level income.

That extra capital is a competitive advantage! Maybe you can afford to make cash offers to drive a harder negotiation and avoid financing fees. Or maybe you can afford a higher down payment to avoid mortgage insurance and having to resort to tricks like owner-occupied financing or relying on seller concessions for closing costs. You may decide that you want to finance your rentals even though you can afford to buy in cash for tax or leverage reasons. But having more money at your disposal is a huge advantage over the young punks out there. Use it to your advantage to negotiate hard, get the best possible financing, and move faster on deals than your competitors can.


3. Take another look at house hacking.


“Forget it, Brian! I don’t want to live in some trashy duplex!”

First of all, there are plenty of upscale multifamily dwellings out there. Don’t discount them just because your experiences with small multifamily properties have been less than thrilling.But even if you are committed to living in a single-family home, there are many ways to house hack. First, you could buy a home with an in-law suite and convert it to an income suite. Could you add an apartment over the garage? In the basement? Something with a separate entrance of course, so you don’t have to mingle with the riffraff. If you have a large garage space, could you rent it out as storage space?

My partner Deni Supplee is in her mid-50s, and she took a unique angle on house hacking. Her children had all left the nest, but she and her husband weren’t ready to downsize from their large suburban home just yet. What did they do? They brought in another child! Through a foreign exchange student placement service, they welcomed a 15-year-old Chinese exchange student named Alex into their home. They fell in love with him, and he’s become a member of their family. And the placement service pays the majority of their mortgage every month.


4. Keep your eyes on the prize: income for retirement.


People invest in real estate for many reasons and in many ways.

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