For example, if in the 30th month I decide to exercise my option to purchase the property, the purchase price would be $180,000 less 50% of the previous 29 monthly payments at $1500 (29 payments x $1500 x .50 = $21,750). $180,000 - $21,750 = the new purchase price of $158,250.

You've got a good strategy there...timing is one of the most difficult things to master in these situations.The option allows you to do the following...contract your end buyer subject to you exercising your option...not subject to the short sale being completed.

That is why I keep adding to it and enhancing it all the time.

That allows you to get out of the deal by exercising your financing contingency.If you're just trying to assign your deal with out doing any fix-up, than the idea is to sell it before you have to close and come up with funds.

maybe its some sort of ancient philosophical exercise

Lets do some exercises. 

They drive to the gym....then get on the stair machine and/or do walking or running exercises.

So for example, if you block out an hour of your day to exercise, then just exercise. 

I realize I could always make a lower offer to enhance the returns.

All in all, it's a great opportunity to create some money for some continuous hard work, it can be done easily, & it will be a win-win for you and your daughter, but caution should be exercised while we are moving closer and closer into a recession.