If you’ve been a landlord for twenty or thirty years, you didn’t just buy a few properties. You built something. You screened tenants, you fixed furnaces at midnight, you learned the hard way which contractors to trust. Those houses are probably your retirement, your legacy, maybe a good piece of what you plan to leave your kids.
And now the stairs feel steeper. The tenant calls come at worse times than they used to. A leaky roof used to mean a Saturday project. Now it means finding someone to climb the ladder for you, and worrying about whether you can trust them to do it right.
You’re not failing at this. You’re just at a different point in life than you were when you started. That’s normal, and it doesn’t mean you have to make any decision today. But it does mean it’s worth thinking clearly about what your real options are, so when you’re ready to act, you’re not scrambling.
Why This Gets Harder, Not Easier
Rental property management is physical and mental work, even when you hire people to do the physical part. Someone has to answer the phone when a pipe bursts. Someone has to decide whether a tenant’s excuse is legitimate. Someone has to keep track of leases, deposits, repairs, and which unit needs what.
As you get older, a few things tend to happen at once. The physical tasks (climbing into an attic, dealing with a flooded basement at 2 a.m.) get harder or impossible to do yourself. The mental load of managing multiple properties doesn’t shrink, but your energy for carrying it does. And the properties themselves get older too. A furnace that was new when you bought the place is now due for replacement. A roof that had fifteen years left now has two.
None of this means you did anything wrong. It means the portfolio that made sense to build at fifty is a different kind of weight to carry at seventy or eighty.
Your Real Options, Laid Out Honestly
There’s no single right answer here. What’s right depends on your health, your finances, your family situation, and honestly, how much you still enjoy this work versus how much it’s become a burden. Here are the paths people in your position usually consider.
Hire a property manager and keep the properties. This is often the first thing people try, and it can work well if the numbers support it. A property manager takes over the day-to-day: tenant communication, repair coordination, rent collection. You keep the income and the equity, but you give up a percentage of the rent to pay for that help. For some landlords, this is the perfect middle ground. It lets you keep the asset and the income stream while stepping back from the physical and emotional labor. For others, especially if the properties need significant capital repairs, a property manager doesn’t solve the underlying problem of aging buildings needing money and oversight you may not want to keep providing.
Sell some properties and keep others. You don’t have to make an all-or-nothing decision. Some landlords sell the property that needs the most work, or the one farthest from home, or the one with the most difficult tenant history, and keep the ones that are easier to manage or that they simply don’t want to part with. This lets you reduce your workload gradually instead of all at once.
List the properties with a real estate agent. If your properties are in good condition, or you have the time and patience to get them ready for market, listing with an agent can bring you the highest possible sale price. This usually means the tenant needs to move out first, or you sell it as a tenant-occupied investment property to another investor, which narrows your buyer pool somewhat. It also means repairs, showings, and a timeline that depends on the market. For a property in solid shape with no urgent need to sell fast, this is often genuinely the better financial choice, and we’d tell you that even if it means we don’t buy your house.
Sell for cash, as-is. This path exists for a specific kind of situation: when a property needs more work than you want to manage, when a tenant situation is complicated, or when you simply want the process to be as simple and fast as possible. A cash sale means no repairs, no showings, no waiting for a buyer to get financing approved. It also typically means a lower sale price than what you’d get on the open market, because the buyer is taking on the repair work and the risk. Deep Roots can make this kind of offer, and when it fits, there are no real estate commissions involved, and closing costs are covered by us in most cases. We typically close in 30 days, often less. But this route isn’t the right fit for every property or every landlord, and we’ll tell you plainly if we think listing it would serve you better.
Do nothing for now. This is a legitimate option too. If you’re not under financial pressure and the properties are still manageable with some help, there’s no rule that says you have to decide anything this year. Thinking it through slowly, without a deadline pushing you, often leads to a better decision than one made under stress.
Practical Steps You Can Take Right Now
Whatever you decide, a few things will help no matter which path you choose.
Get a clear-eyed list of what each property actually needs. Walk through each one, or have someone you trust do it, and write down the roof age, the furnace age, any known issues. This isn’t about scaring yourself. It’s about knowing the real condition of what you own, instead of a vague sense that things are wearing out.
Talk to your tax preparer or an accountant before you sell anything. Selling investment property can trigger tax consequences depending on how long you’ve owned it and what your basis is. This is worth a real conversation with a professional who knows your full financial picture, not a guess based on something you read online.
If you have family members who might inherit these properties, have an honest conversation with them now. Do they want to keep managing rentals someday, or would they rather see them sold? This can shape whether you sell now or hold and let it pass through your estate.
Consider talking to an elder law or estate planning attorney, especially if health is part of what’s driving this decision. They can help you think through timing in a way that protects you and your family.