Hiring a lawyer sounds expensive, but it is way cheaper than hiring a amateur (in this case yourself) who costs you money and provides no results (and then you need to hire a professional anyway).My personal philosophy is to "do it right, or do it twice" and its way cheaper to do it right once. 

He is very good about deductions on tax returns so his income looks negligible and of course banks wont talk to him about loans.

Now consider this: all the groups people are spending fortunes to target—foreclosures, absentee owners, probate leads, tax liens—what do they have in common?

Lower taxes, no POS and lead testing. 

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Investors often obsess over how to defer tax obligations and ultimately make poor investments due to being hyper focused on taxes.

You did purchase the property in one tax year and are selling it in another tax year which satisfies one of the court rulings. 

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

He is a realtor that I previously purchased a small portfolio from and therefore had a good professional relationship.

You get your tax benefits.