And Jerry is a Wyoming attorney, so you can trust his legal advice! 

I have done extensive research in the risks, how to structure such deals to mitigate those risks as effectively as possible, and legal considerations of each strategy. 

I consulted with a real estate lawyer a few times this year who said it's very hard to sue for negligence and they advised against taking legal action, especially since the property manager at least followed through on the eviction and repairs.I've now asked the property management company to apply a $4k credit for all the challenges I've had working with them.

We aren't quite there yet, still finishing doing some restructuring.

If a guest stays for one week in July, the owner can't legally rent to another guest until August and must leave their unit vacant for three weeks.

And never being “at risk” is it even sufficient to legally bind a seller?  

If you don't sign the contract and hire that agent, then they legally shouldn't be working for you.

But for large multi-family, that amount hardly covers your legal fees for one transaction, let alone down payment, due diligence costs, lender fees, other closing costs, etc.

At the same time, someone else reduces your debt, and you get to use the tax code to improve your tax situation legally.  

I was one of the fortunate ones that was able to get out of the contract and after all expenses (forfeited deposit, legal fees, holding costs, etc) lost less than $20k.