I'm trying to decide the smart investment decision - continue renting it out at a lower rental rate OR selling it and trying to find a potentially better performing asset to re-invest those funds in.  

Some of the negative reviews I've read on Norada (not necessarily on BP) seem to stem from not understanding Norada's responsibility in helping you meet your investment goals, nor in yours once the purchase contract is complete.

You can (delicately) begin talking to these tenants now that you're in contract.

Is the mentor going to actually walk the deal with you, negotiate contracts with contractors, etc with you?

Switching property managers seems like it was a smart move, especially with how much you and your wife had to step in before.Chicago definitely isn’t an easy market, but it sounds like you’re set up for better success moving forward.

"A smart person learns from his mistakes, but a truly wise person learns from the mistakes of others" - Ken Schramm

How would some of you guys go about drawing up a contract between us and the family member. 

Most fail to paper the contracts, indemnification and additional insured requirements correctly.

However, repairs or improvements must be permanently affixed and add value to the real property.Costs and Escrow AccountsThe costs of the renovations will be based on the plans and specifications for the work and on the Construction contract for all of the work requested by the borrower.

Knowing this information will help you identify the right professionals to bring on board.At minimum, your team team should include:Financial Advisor: to help with investment strategies - portfolio diversification and risk management.Real Estate Agent/Broker: to help with property acquisition and market analysis.Accountant or Tax Advisor: to help manage financial records, tax planning, and optimization.Attorney: to provide legal counsel for contracts, agreements, and investment structures.Mentor or Coach: to offer guidance, insights, and industry knowledge.Networking and Relationship Builder (for everything else you will need): to connect you with potential partners and collaborators.