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. 

At this point we are not able to find a solution except that we need to hire a lawyer which will add to the cost.

My wife and I are considering taking on this role as a property management team, managing these properties from our current location in Washington state.Our plan is to establish a reliable network of local contacts in the area—such as maintenance professionals, agents, lawyers, etc.

My wholesalers lawyer says he has "cloud" over the property which keeps the original seller from selling it as you stated.