I empathize. I've been managing (and working in tech until last December as well) a 20-unit building for the past 30 years. It's family-owned so I'm highly motivated to maintain it well, but it's way more work than anybody I know realizes.

I just wish we had mandatory courses in high school for kids on stuff like this. Hiring good realtors, alas, isn't the answer as their goal is to sell not give you reasons to reconsider or add caveats to simple leases, which take extra time to negotiate.

There is no substitute for a basic education in home buying that is geared toward helping the buyer. In addition to teaching kids how to invest for their own retirement, this really should be on the required list for a diploma--what good is calculus when you can't calculate your own living expenses?