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. 

Are they a pain in the butt? 

I wish I had that in my first years and I am sure I would have avoided some pain and loss. 

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

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.

A lot of landlords, especially mom and pop landlords, have pain points and struggles in being a landlord.

Holding onto a HELOC long term is painful, so you'll want to make sure your exit from the HELOC is planned out. 

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

I think 1 commercial loan is way more pain than 1 sfr, but 10 commercial loans is way EASIER than 10 SFR. 

She has some bigger psychological issues and my rent is not high enough to deal with it.