@Emily Ellis I'm not a lawyer, however several properties in my area I found thru 2 separate wholesalers, turns out they were marketing a property which was listed on the mls and they were "in contract" which was bs, ended up one of my agents brokers were the listing as g ed NY and pulled the the excepted offers from them.

Once in my control I would get the lawyer started on the deeds and agreements, and the realtor started marketing the property.Option 2, is an idea that I have only been thinking about recently.

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.  

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

Getting prelims from an Escrow company or Lawyer is great.

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

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.

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

I hope you consulted a lawyer before adding that out clause for yourself.

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.