I have two applicants. I like both, have run background checks, and there are no red flags.

Candidate 1: financially a little better off, and I believe will treat the house very well. Due to their family situation ...

If you don't mind me asking-- which strategy did you choose to get started and how did it work out for you ?! 

I think combining both properties on one deed would be beneficial to any exit strategy.I know I came off harsh and apologize to @Shawn Holsapple for that, but it is definitely not a path I would choose. 

do your due diligence and then go for it...whichever way you choose to go will be a winner.  

However, unless you're talking about an FHA or otherwise government insured mortgage, lenders are relatively free to structure their agreements as they choose. 

Either way I choose, he will deduct that from the cost he charges for closing on that property. 

Just choose your comps carefully, allow for differences that affect value &/or desirability, and you should be good. 

If they are wholesaling the deal they may choose to double close which means they actually buy it and then resell it to you.

If you are living off of any of the current cash-flow, then that will be a consideration of how much financing you will choose to place on the existing property.

GabeI am curious, what did you choose to do?