Does email work for that though, since it's at least documentation?

Except that you have told her that she can stay.If you want to give an incentive, I would document a few options on paper, go talk to her, and leave the paper with them to consider their options.Is the house likely to remain a rental, be owner occupied, or could go either way?  

This theoretically triggers a default clause on the loan document, but as the mortgage will stay current, lets assume nothing happens.5.

Would the loan be possible without any other documentation?  

If you can are comfortable with the other documentation, and they can afford the rent based on their income, and you're comfortable with their credit worthiness, what's the problem?

Take lots of pictures, document everything you see and find and keep all receipts for repairs, cleaning, etc.  

The lack of attention to detail is one thing that has cropped up time and again, but also the reliability factor, and principal-agent issues (ie: our person doesn't care as much as we do and doesn't document their work, etc).  

From my research, it usually costs a minimum of $10K (and sometimes several times that) for a securities attorney to draft offering documents (PPMs and the sort) for real estate syndications, which means that deals below a certain threshold don't make sense to syndication because the cost of legal fees eats into the deal too much.Is this a legitimate pain point?

In my experience, Declarants-in-control have a tendency to over-pay management companies, sometimes even management companies that they own under separate legal entities.If you were successful getting much information from a HOA as an offeror, I am impressed, as their governing documents and practices generally limit their obligations to their own Owner/Members.  

Rate is 8.5%, loan term and amortization is 30 years. 4% origination fee, flat document fee, and that's it.