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. 

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. 

It seems like they all want to charge for ACH and Credit Card Payments. 

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.

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

I can have them just setup an ACH for the monthly payments, etc...but I feel like this would be easier with some automation, and there just must be something that's already setup for this.

Norada’s promissory notes generate predictable monthly passive income transferred to the investor’s funding account via ACH,” ( Link ).Santarelli confirms these fixed, double digit returns in a detailed YouTube video presentation (Link, at 35:08).

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