while i understand the answer will be different for each investor, I am wondering what questions I should be asking myself so I can come to a rational conclusion. 

Speculation isn't investing (it's guessing with style), and rationalization is very expensive.

Most empty nesters move out of the nicer parts of Nassau anyway because at some point you just can’t rationalize paying $35k a year in taxes with no kids in school. 

You'll end up rationalizing your way into bad (very bad) deals that will have a domino effect on all future deals. 

@Brian EllisThere is one major reason for thIs - your price is too high. stop rationalizing it and losing money waiting around .Drop the price and watch what happens

Stop rationalizing.. your price is too high so drop it 

My rational is that he would be financially invested and have more motivation to do a good job and meet deadlines.We agreed to set up an LLC try 3 flips together.

Buyer 1 receives this information and is asked if he is willing to offer more and realizes that it will cause high default chances if something goes even slightly wrong, and rationally says no.The other seller in the area raises price of MF2 based on the fact that MF1 sold for 20% over asking price.

Make sure you follow the required steps in your local laws regarding this...and DON'T skip, rationalize, or in any way deviate from those steps in any way!!!

(Irregardless of the actual law, it would arguably make total sense if the landlord could keep the deposit until the end of a fixed term lease, as security for the outstanding rent payments that the tenant is obligated to pay; but what makes rationally sense is a whole different topic as laws not always make sense.)