Our roof is leaking and to continue to have homeowner's insurance we must replace in the next 3 months. I have a family member who I would like to have do the work as he will charge me a lot less than a regular roofing contractor. I will be buying the materials, but then I will be paying him cash. There probably won't be a contract, however, I could save the receipts for the materials and dumpster rental from around the same time which I feel would explain the circumstance. Any thoughts? We will have to wait to file for awhile after to save up for the lawyer because I do not want to file pro se. If it would be a big deal, than I will try to hire a regular roofing contractor instead.