I've generally gone out for those sorts of trips unless you really trust the team to have a sharp eye as a lot of the styling happens once everything arrives and you have to make it fit together. 

Are they a pain in the butt? 

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. 

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.

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

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

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.