If you're comfortable with everything and just need help to negotiate a fair arrangement, then hey, it is your money and your decision.

I've arranged a tree magician to make it disappear next month.

Legal Zoom and Rocket Lawyer can put together a bare-bones agreement, but they usually don't hold up well in court if there are numerous partners or special arrangements, which is what it sounds like you have.

I'm an appraiser, contemplating getting my brokers license. or getting my sellers license.

I agree...not sure about your state, but, if you don't have a payment, partial payment, and/or specific payment arrangements with explanation of when and where the money is coming from by your due date or grace period, let alone 2 weeks into the month, you have to start the process....In CA we give them the 3-day notice to pay or quit, that has to be non-responded to before we can actually file for the eviction, that cost another $500+ depending on if they dispute it.Of course, you should try and talk to them and gauge their intentions and let them know yours before any action.

When they contact you ( and even the tenant that’s gone dark will call) to make arrangements to pay you can negotiate whatever deal you want wave or keep late fee, (if they can’t pay rent a late fee is useless.

I'm in this pickle right now where I'm sitting on a pile of cash and contemplating each of these options.

Most room renters are that just to get cheaper living arrangements.

In my market area, good contractors are so busy that I would expect this arrangement to play out with the contractors telling the tenant when they are coming, and the tenants will have to rearrange their household schedule to accommodate him.Option 2: Tenants acknowledge that they will trade their discomfort with a tradesman in their home when no one is home for the convenience of having the work done in their absence and not having to live in a construction zone for several days upon returning.I agree with what Account Closed said. 

I house-hack over in Village 7 and it's been a phenomenal arrangement so far, good luck!