First of all, I am sure there are some key learning opportunities you took away on properly vetting tenants and figuring out the Chicago Landlord-tenant ordinance (i.e, move-in fee).I'd just talk to your tenant first and see if he can be reasonable, then resort to cash for keys.

You would only pay him when he has successfully completed a phase of the work satisfactorily, including inspections where applicable.Secondly, if you have a proper contract, it will be easy to just suspend the work, fire him ,and hire another Contactor.

I'll post an update if I ever actually get it installed.

@Brendan Seals a new AC/Furnace here for that size house recently cost me 4k and last month I had a new 40Gal. hot waterheater installed and it cost me $1000 (which is up 20% over the last  year).

Just the rock on the roads without my bill was $25k, the septic system I'm installing in almost $100k.

Take ownership of your mistake and learn to do the proper due diligence recommended above😊

Additionally, a good broker will make sure someone buying a $1.2MM property is not a tire kicker, and has a preapproval or proper proof of funds. 

My plan was to sell the property next year, but wanted to pull some cash out prior to selling to help minimize the capital gains tax.Is there a proper name for this type of loan product that I should be looking for?

Both fair and properly incentivized in our minds.

For $50 and an hour of time, repainting is no big deal.If you want a more lasting solution, install composite decking.