The two of these sort of deals I'm in had a significant amount of paperwork, comparable to closing on a house, when the money actually changed hands.

A 75/25 split... if profits are 40,000 you get 30,000 your partner gets 10,000.Compare to 20% of 40,000 = 8,000, leaving a balance of 32,000 to split 50/50 or 16,000 for your partner and 16,000+8,000=24,000.. which would you rather have. 24 or 30?

Short sale is not an option for him as his primary motive is to protect his credit - which he needs for other purposes.

Just from the results, after applying the rule, looks like option A is better, but I don't think you can compare a property that rents for $500 with one that rents for $1500.

Due to fha guidelines this income is not included for debt to income purposes and therefore im only qualified for 125k loan with 20% down.

The economy here has done very well compared to most other places 5% unemployment rate and while yes the job people want may be hard to get most people still have jobs.

Is there any way to compare prices of homes with and without it in your area?

I have no experience with the software but here are a few forum posts comparing and reviewing it:http://www.biggerpockets.com/forums/79/topics/44375-freedom-soft-anyone-plan-on-purchasing-it-http://www.biggerpockets.com/forums/79/topics/91576-would-like-opinions-on-freedomsoft-program-offeringhttp://www.biggerpockets.com/forums/79/topics/67210-realeflow-open-road-3x-versus-freedomsoft-vs-sims-20http://www.biggerpockets.com/forums/79/topics/83761-my-review-of-investorpro-vs-realeflow-vs-freedomsoft

For tax purposes I am going to have to make some purchases though before years end.

That term, for tax purposes, refers to someone who buys and sells property as a part of his or her trade or business.When doing lease option assignments you never take ownership of the property, so the term would not apply.That being said, income from lease option assignments is considered ordinary income and is taxed as such.