I prefer one person to be the primary resident/ responsible party.

Where and when is the party to talk money !!

In my opinion, I would much more be interested in receiving a small amount to flip, make profit from and return the amount in whole within terms of a legal contract between both parties.

@Roberto Vasquez, A 1031 exchange is an entire process that involves the use of an unrelated 3rd party called the qualified intermediary whose sole job is to document the sale and purchase transactions and to hold the funds inbetween. 

You can't get that if the applicant submits a third party app. 

The party thing is already being dealt with by AIR, VRBO, and cities themselves.

However, we do tend to get quite a few bachelorette parties/girls trips/couples trips when we go to a two night minimum.

However, as you said, it is dependent on the terms of the loan and/or contract with your counter party.

Any insights on how to make this deal work for both parties?

Did you have the parties sign an estoppel agreement?