.*  Roth may win here, but that income offset is sort of nice.* Before everyone piles on about RE Pro (yes, that is one way to do the offsets), realize that at the disposition of an asset, Cap Gain unlock passive losses to be used against all income. 

As the market has changed the last year, I've still managed to find great deals and I know how to win offers.

Don't pay the credit cards and don't take their calls.

Other debts include a little credit card debt that he has, small auto loan of mine, and my student loans which equate to $9,240/year in required payments)So, the HELOC loan officer was useless and told us she is frustrated with her job and basically dislikes her UW dept. because they work from home and she doesn't get to.

For example, they may not have an SSN or a driver's license, so I take passports or green cards for ID.

You must understand the rules of the game you are playing if you want to win. 

With some creativity and an open discussion of her needs and you being aware of your numbers you may be able to find a win-win. 

Win-win.  

Any advice on how to come up with a top end bid that will win me the this opportunity while still being able to make a good profit?

Also when it's all said and done he needs to have a case to get anywhere, meaning even IF he were to sue you he would still have to win.