Him potentially having to move, uproot, pack, find a place to live, etc. is threatening and unfamiliar - you both know why you're there, you'll get to that topic eventually.Do not talk about yourself.Once you gently meander through the 'genesis' convo, bleed in to asking him what he values; that's the question, and pose it genuinely, "I would love to better understand what you value...and what's the best example of someone exemplifying that value to you?" 

Literally, rather than rent the place out (or sell it... some comps are sitting on the market for months and months, AND he feels that the market is likely to bounce back), he believes, and I think he is reasonable in his belief, that it is best for him to simply "bleed" the $2,000 per month cash flow loss covering the spread between current rent and mortgage/HOA + maintenance/CAPEX and wait for clarity to emerge. 

But your partner who brought $10k to the initial closing and then $5k for the roof demands to be paid his $15k back IN FULL - or else he will not sign off on the sale, and you will continue to bleed monthly mortgage payments.

You know what they say, "If it bleeds, it leads...." 

one reason is most are bought with as little equity as possible and if you have a vacancy factor that causes bleeding dollars its not long and your toast..   

Let your heart bleed for them !

First, we're locked in with these tenants till summer because of leases and we'd bleed money with the current rents with a conventional note.

Great to meet another NC investor, lets unpack this a bit.1) This answer may bleed over into other questions, but you should be financing this property.

With prices swelling everywhere we might look at some of those midwest markets a bit closer@Harrison Sharp @josiah

3 bed 2.5 bath, ~1800 sfMajor exterior remodel due to that old nasty LP siding that swells and absorbs moisture.