Reading that was painful.

Are they real pain to renovate?

I even done that when I had the C Corp management company which I used for tax purposes, back then before Obamacare, I cannot pay my health insurance as a real estate expense, it all went through the management company which has a policy of covering it's members health insurance co-pay etc.

The last thing you want is a tenant claiming health issues due to improper asbestos removal. 

Dad is 72 and mom is 71 with poor health. 

Some hard money lenders can be a pain to work with and some are a breeze.

I know I'll be subject to self employment tax & paying for health insurance out of pocket (versus the group plan I get through my job) - what other expenses or considerations should I factor when looking to go this route?

Training someone on those platforms would be a pain.

Education needed a kick in the butt to straighten out some issues, and it's going to be a painful journey for a while ( years, likely) but in the long-run there can be major strides forward to mix the mandatory need for tech. education vs.  

We recently rented a vacation home that was pet-friendly, and we were required to provide a certificate from our vet attesting to the good health of our pet (I believe to ensure that he was fully vaccinated).