Some contractors weren't great about writing detailed invoices so in some cases all I have is a large check written to 'roof guy'.So.... question: is there alot of scrutiny from the IRS as to how you determine the basis?

Consider your long term strategy/goals (write one out if you don't have one).  

Thanks for the detailed write up! 

Definitely not writing off Memphis and always up for some convincing.

Sit down at your computer and write your rental criteria down.

I am writing to you randomly and ready focus with my full potential!

In other words, write that gift off in your mind so that when they stop making payments or the litany of excuses starts, you've already accepted it as a loss.And if a bank will not lend to them, then I think you have your answer - and hopefully you can blame it on your "partner".

I have a blog where I write about Real Estate  www.homebestchoice.com and I welcome you guys there too if you would like to share experiences and tips, would be a pleasure to have anyone's help on it. 

@Jake Thomas, I think I am leaning towards writing my own purchase agreement that is very simple and easy to understand for my customers.

Write the HOA .