I'm Jessica, born and raised in Rochester, NY, where I enjoyed playing soccer and lacrosse.

@Marko BukvaI'm not entirely clear on the plan and ownership, but there are potentially several different types of tax at play for a transaction like you're discussing - gift taxes, estate tax, income tax, property tax, documentary transfer tax, etc. 

However, I received some feedback from one of my partners that the play here would be for an investor to subdivide or re plat the land for a multiple tenant situation.

Do some digging to see if there is something more at play or if he is just being difficult because he is a difficult person.

One small point of criticism; we were there in the winter and in the evening a lot to play a game or watch TV.

To play devil's advocate (and keep in mind I have no skin in this since I'm in a different market):-You want to tailor to investors, then be prepared to sell at an investor price. 

Look, we were for most part playing a game of American Football for a long time.

Divorce - its easier if the house is in the divorce decree otherwise you need to play mediator between parties to come to an agreement. 

Selling means giving up an incredibly cheap cost of capital, especially in an appreciating area like 28277.I direct my investors to 28277 all the time for appreciation-focused plays.

Here is my Cliff Notes on this elaborate example:If you have unused losses from the past, they might significantly soften the tax blow from a profitable sale.I don't see how this is called "strategic play" or "premium lemonade."