Thank you, very helpful information, have been routinely excluding properties with HOAs in my deal search just because the major cash flow hit, but will incorporate this advice and maybe start looking at some properties with HOAs as long as numbers work out and HOA governance/regulations are favorable

But meeting a few handyman's, this would be important.Plan on making routine trips to visit the properties. 

I am starting to feel very uncomfortable and am wondering if anyone can give me advice on how to handle this situation.

Most bidders bringing cashiers checks feel uncomfortable without knowing the inside condition.  

If they're the type of people that you feel uncomfortable giving your DL to, you probably shouldn't be renting to them.

We routinely see bad bookkeeping, questionable (or optimistic) rent rolls, and all manner of numerical freewheeling in financials, so make sure the numbers are accurate, and then, check again.  

I found it works well as it puts a subtle message in their minds to either check out on time or we may have to have an uncomfortable phone conversation. 

I prefer to be transparent and honest with people, even when it means having uncomfortable conversations.

If you are uncomfortable doing a complete inspection, pay to have one done and then sit down with the seller and go over the details.

I think it really is about creating a routine to get the most out of the time you do have.