Jeesh Reader, I didn't realize that this was a contest. I'm quite happy with my station in life and hope that you are too. As blessed as I feel, I rarely have to look far to find someone with more wealth and I like having wealthly friends.
I'm not sure what any of the first part has anything to do with holding rental real estate in retirement and the issues that I raised of time involved, being "on call" and lack of diversification.
My dad was very into real estate. He had a number of commercial rentals when I was young, many pieces of land, and later some residential rentals and another single tenant commercial rental. He came to view the residential rentals (an 10-unit apartment building as I recall and at least one SFH) as a PITA and sold them. I am eternally greatful to him that he sold out of pretty much everything other than the one single tenant commercial building.
While I doubt that I would have chosen that path it really wasn't an option for me because of the hours that I worked and the extensive travel that I had with my career.... I just would not have been around enough to invest in rental real estate.
I have no doubt that real estate is a great way to build wealth, both dad and uncle did very well with it.... it just wasn't for me. However, to rely on real estate in retirement becomes increasingly difficult if one want to travel a lot or does a lot of their own repairs and maintenance work.... even thought the cash flows are quite attractive.
I dunno, pb4uski, maybe it's your tone...
Your dad did a great job of setting your mom up for a secure retirement with the wealth he built in real estate. For THAT you should be eternally grateful. I don't know what he did for a living outside of the real estate, or what opportunities you had that he may not have had. That may have determined the path he took. Whatever the reason, the real estate probably improved your opportunities as well. It was a successful path for your family, and that's what matters.
I think most people here with long term experience with rentals are well aware of the issues around how to deal with fully depreciated assets that have dramatically increased in market value. The answers are different for everyone. Sell and take the hit, exchange into something less management intensive, or outsource and accept the frictional losses of letting someone less interested in maximizing revenue while minimizing losses take over. Those are pretty much the choices.
And the Flint Michigan example of which you are so fond? Astute people take the loss early and move on. In equities, you diversify to avoid the Enrons you can't foresee and hope the returns on the larger portfolio outweigh the losses. In real estate, you can spot the losers and cut your losses.
So, maybe take the edge off your tone, and recognize that people, many of whom may not have started where you did, have accomplished a lot. They are not stupid. Most of them are certainly smart enough to spot the Flints. Remember that for every Flint, there is a place with an appreciation rate well in excess of inflation. Add in astute use of leverage, and some people have done very well as a result.
Maybe include the pluses as well as the minuses of real estate when you offer your advice, especially to people starting out. They might be more inclined to listen to your advice if you did.
That is all.