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. 

So at that point seller is losing money..

There would only be about 3 active players with the rest being "passive".

You lose your economies of scale.

It's the worst or best (depending on your strategy) boom and bust real estate market in the world.The explosion of the last bubble during the financial crisis was much worse than the US, with some properties losing three quarters of their values.

I wonder if going heavy into the "gaming" look may lose my credibility, however a nice touch of it will say that you're there for THEM and the industry.

That's a great way to lose money!

In the meantime, maybe to keep your current bookings in place and not lose that income, you could work with a mediator to explain that you will seek a full time renter after these current bookings have transpired.