Is he in good health?

I want to try and solve a painful problem before the offer. 

I take credit cards, too, which are a bit of a pain and still charge as much as Airbnb does.  

Currently, one of my long-term employees is on the brink of financial bankruptcy due to the significant health care costs associated with her teenage daughter’s severe mental health illness.

If you don't take that seriously the experience can be a painful and expensive one.

If it matters to any degree to retain this tenant, if listing for new tenant is a pain, I'd simply call this guy up, I'd be upfront and ask him about all this.

It waives nothing, but says you aren't going to be a pain and are only looking for major items.If you are losing to inspection waivers, you might not be looking at the right properties.

And the health dept (i.e septic permits) is down about the same if not a little more. 

Hot tubs are expensive and a pain in the butt.

Last piece of advice is to raise additional capital because shortages while building ground up can be a painful proposition.