It's usually pretty close to a wash, or when I hold the rate constant it's like 20 basis points (to price, not to rate) or something trivial, coin toss which will win on any given day.I prefer to have my direct lender hat on to my broker hat when working on REI deals (not licensed in your state, don't actually bother PMing me) because your situations are always wonky and I need that direct telephone/IM/email line of communication to the assigned decision making underwriter so I can go over your net loss carryover, or weird Schedule C, or funky deposits, or whatever it is, with her and get it resolved in 5 minutes rather than over the course of 5 days of emailing back and forth through some intermediary. 

Nothing personal but if you do let him stay, increase the rent and add the difference on the security deposit.

You have already collected a deposit from the new tenant and now what do you do?

Also, explaining all the sale prep, your schedule, and how they need to be vacated may help as will a mention of the deposit return (for an empty intact property by the specified date)..If you sense resistance or an issue or have a question, you could get legal advice.

We did not enter into a new lease agreement yet with the "new tenants" but we have talked about move in dates and deposits and prorated stuff. 

Hate to say it Chris, but sometimes peoples goals and ideas just don't match up.  

Correct me if I'm wrong but it sounds like your shopping for terms deals that are already advertised as such, most likely buy other investors who want an option deposit.

Your tenant moving out, and some damage beyond their deposit and a furnace fail.

They tried to use another cover but cannot find a match.

So what if you lose your security deposit?