Once a landlord backs down from any ultimatum, they lose credibility.

At some point during this process they will realize they are going to lose and might ask for cash for keys, as long as that is still a cheaper option VS continuing the court case, come up with a number and go. 

If they aren’t and you don’t want to lower the price you could risk losing the sale and have to look for a new buyer which would increase your holding costs.

If I was losing cash flow on one deal I was going to pick it up at another.I bought a run down legal 2-unit for $392,000 and put 25% down and $50k into it.

Sure, it is nice to keep everything in perfect order, but you'll lose out as a landlord fixing this stuff.   

Would that roughly translate to me losing roughly 55% of that or $2750 when the property gets sold?

You can walk away from the deal before end of the due diligence period regardless of the reason, but you will lose the money.  

Somebody will make him a better offer in which case you lose nothing because you have no money at stake.2). he will take his home off the market in which case you also have lost nothing3).

@Christopher HelwigCo-mingling funds and using the LLC as an alter-ego are surefire ways to pierce your corporate veil and lose your limited liabiilty protection, the main purpose of having a LLC.If you want to "consolidate" your activities, I would transfer Title from yourself to your LLC (same or new one which is whole different discussion) and simultaneosly refi into a commercial loan since legal entities are not eligible for residential lending (hopefully you aren't "frankensteining" it).Hope that helps. 

The closer I get to $100+ savings, and the more offers I lose, the more enticing it is to try my hand at a legit BRRRR.