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

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.

It pains me to hear what my fellow landlords are going through.

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

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

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

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

I think your post is valuable feedback consistent with the spirit of this thread in that it indicates what some of your pain points are/were so that others can both make informed decisions about their own investments and also so that the Morris Invest team can continue to hone their services to be the best they can be.

Capex and tenant issues tend to exceed cash flow and when you decide to exit after a couple of painful years, you are in for another surprise:It is shockingly hard to sell cheap homes!