Years ago, my elderly neighbor expressed his concern to me about our trees leaning towards his home and that he wasn't trying to be a pain. 

Also, any advice for avoiding those unexpected surprises (or at least making them less painful) would be super appreciated.

Are you doing butcher block, quartzite or masonite for counter tops?

A 1031 exchange is NOT available for owner occupied property so that’s the bad news.The good news is for owner occupied primary residences, for married couples, the first $500,000 of pain is tax free.No need to worry about a 1031, live in the house, sell it, use the $500,000 exclusion and you pay KP tax on whatever profit may exist,2.

Don't buy the cheapest Amazon sets as it's a pain when they inevitably break.

What pain points or problems have you encountered or seen when evaluating real estate deals?

It looks as if they hired out to H&R Block and didn't bother to check their math. 

have seen this play with eastern Block women . 

If you want a city, Philly can be done if you know where the blocks break.

I live 2 blocks away :)  I had another one in Portland proper same thing you could not get in it stunk so bad you could smell it from 15 feet away as you walked up..