Tax Implication Question - Profit from Sale v. Assignment Fee

[Wesley Wiliams]

In trying to think about structuring deals with potential motivated Sellers, what is the difference in tax treatment for profit from a sale (in the case of equity over mortgage balance) as compared to payments received from am assignment?

Generally, would it be preferable for a seller to discount the sale price in exchange for receiving a share of the assignment via side letter agreement for an assignment fee split agreement?  

The factual scenario would be: Seller owes 40k, I offer for 60k, how ARV is 100k, wholesale sale for 80k. If Seller lowers sale price to 50k and I offer Seller 10k on the assignment, such that Seller signs sale option at 50k, I sell to Flipper for 80k and pay Seller 33% of assignment fee (10k at the 80k wholesale price or lower if wholesale price ends up being lower) of the assignment fee. Is Seller in a better position for tax purposes than if Seller had sold at 60k?

I ask the question because this could be a strategy to get Seller to have skin in the game for the assignment and work with me on price and it still allows me to reserve downward negotiation on the wholes sale price. 

Even if taxes come out in a wash for the Seller (I.e. It's the same tax treatment, it could still be a good strategy to negotiate down price and sign the Seller-side deal. 

Thought I'd pose this question to the group.

Thanks. 

Wes