This counsel is not necessarily the lawyer who does your closings--look for expertise in company structure and litigation all with knowledge focused on real estate or development.  

Most S8 tenants have a history of bad decisions, often having convictions, evictions, bankruptcies, chargeoffs, collections, garnishments, etc.

Is there any flat fee lawyer in Chicago that can help me file this?

Getting prelims from an Escrow company or Lawyer is great.

The company went into Bankruptcy and the BK judge ordered that the majority of the lots (about 3,800) including ones already sold and many built on; be organized into one brand new municipality. 

I'll chat with a local lawyer and see what they think. 

The rule I use is to double the money after five years in case you need to sell.Meaning, with your initial investment of 132k (down payment plus initial closing costs), and considering an additional 5% closing fee of the home’s value when you sell (roughly another 30k for agent and lawyer fees), your total upfront cost plus closing on sale would be around 162k.

Are there general rules that apply about this, or is this a lawyer question?

You would need to consult with a lawyer to set the trust up and ensure the best protection for your situation, and then relay that information to your tax professional. 

I'm sure they'll just make sure the company has no assets and debt, so when they get a few million dollar fine they'll just have the company declare bankruptcy and dissolve.