You need to be careful handling the transactions, like not depositing checks in your regular account and then transferring to your Roth.

It might require a security exemption, however, which is something you should check with your attorney.If legal in your state, you can fractionalize your loans -- also called a multi-beneficiary loan.

Check out meet-ups in your area as well.Good Investing...

If that happens, check with your agent about insuring the property on a Commercial Insurance form (Business Owners or Package policy).  

Check the Chicago laws to see what your  options are as far as saying no. 

I want to use maybe the first dozen jobs or so as free labor for the customer.

Check with your lender, but the 203K requires work to be done by professionals (at least the major stuff required for them to release funds) to be done within a certain time period.

Check with a local title company and ask if they'll insure title and if so what would the requirements be. 

3) Check out some of the local meetups that you can find in this forum!

I'd be happy to meet you up there if you want to check it out!