Wow, as a landlord of several single family homes I am amazed by some of the posts that say their rentals have been "no trouble." Seems incredibly lucky. We've been landlords for 45 years and have put on new roofs, A/C systems, water line replacements in homes built in the 80's, etc, a new sewer line on a home built in the fifties, as well as the usual carpet, flooring, water heater, appliance replacements. And used gallons and gallons of paint. My husband is extremely handy and has saved us thousands in repair costs, and I have definitely put in my share of the work also, as well as doing the bookkeeping.
We had a condo unit (won't go that route again) where the tenant accidentally set the place on fire and we were so lucky it didn't hurt anyone or hurt any adjacent units. We had a single family home that also caught fire and luckily no one was hurt there either. Now we are at retirement age and are thinking of selling one per year going forward, but have also considered just keeping them til we die to pass on to the children for them to sell. However, we would definitely need to start spending big bucks on cleaning, repairs, etc that we have been doing ourselves, so maybe it would be better to sell, pay the taxes, and invest elsewhere.
Repairs and liability is what I would be concerned about, going forward, if I were the OP. We are in our upper sixties and [B]what you can do at 60 is very different from what you can do, or feel like doing, when you are close to 70.[/B] Just because you have had few repairs in the past doesn't mean you won't have more going forward as the building ages. That said, we traveled 75 days last year (not consecutive) pre-Covid and were able to manage the properties by phone. This year of course we haven't had the opportunity and not sure when that will happen again! Have been spending a lot of time on one property that is run down, getting it ready to sell. Not sure how much more of that we want to do.
I would be fine getting a property manager to manage, but if we have to pay for all the cleaning and repairs I wonder if it wouldn't be better to sell a home per year and pay the taxes. It's a conundrum. Have also looked into DSTs, though there are definitely fees associated with those, and quite a few DSTs are retail. Retail has taken a bit hit this year.