Let him exercise the "happy clause" of the Lease.

This is a bit of an odd situation so it's not something I will deal with on a regular basis.

Especially if you live in an area with regular freezes.

What happens if it doesn't sell for months after they finish; they are going to be calling you regularly asking for their money.

In my town the likelihood would be the inspector was looking to be greased, they get led away in handcuffs regularly.

I don't know why your oil boiler is a PITA, but regular service from your oil supplier is often free, is it being serviced yearly? 

Nothing would be a deal breaker alone, but factor this level of expertise in when evaluating the complete picture.For example, a big problem that I've seen is if a single tenant building is applying with a regular lender, sometimes they apply a vacancy to their own DSCR (Debt Service Coverage Ratio), and they apply a vacancy factor for a single tenant building, which is just wildly inappropriate.

Remember relationships are built over time, so it may take 3-5 years of solid membership and interacting with your bank before they know and trust you enough as one of their regulars.

Schedule open houses regularly (believe it or not, I schedule daily showings at a fixed time) - Your desired tenant is probably looking at other places so make sure they can see your house when they are available.4.

At this point, I think analyzing this property is more an exercise in education than anything else.