So lets say its a $1M loan accruing 12% and I pick it up for $800k (or 900k), time could be my friend or my enemy depending on the value of the home.

Some areas/neighborhoods are more STR friendly than others. 

Sounds like your friends didn’t do their due diligence...

One of my friends uses comped quarterly cleaning as their inspection day and trains the cleaners to take photos and videos of everything.

Having said that, before you dismiss a sponsor for violating this guideline, take some steps to ensure you are communicating with the right person, and that communication is actually established.

I ultimately decided to look out of state where the price points were more affordable and the numbers made sense + landlord laws are more friendly. 

Don’t talk with your spouse unless they want to, not your friends or coworkers, not your family.

Since my tax guy is of no use, I reached out to a friend who works for a different tax group/CPA and this new firm was kind enough to look into my predicament.

Partner up with a friend and buy one together a be roomies for a year. 

We have a friend that is local that has offered to show it for a small fee if it comes to that.