In MA, you can usually get insured with Fair Plan with certain pets, but it is VERY expensive.  

Charge extra for an ESA.

When most people say don't buy (like in 2009), it's usually a great time if there are strong underlying fundamentals.

Would the person who takes on more labor to repair the property have greater preferred equity or is this usually treated differently?

Windows would be my next check-point (less than R1) and then wall insulation: I would not be surprised if they have no insulation inside, but you can do blow-in, which only requires a small hole.A home looses heat in two ways: heat conduction (which you can slow down with insulation) and drafts, which in old houses is usually the biggest culprit.

You'll likely pull a few hundred extra dollars and will will get shorter leases that could work better for your traveling.

I think it's going to be location specific for sure; where I am very few people hang out in the house all day long as they are usually busy hitting the parks and attractions. 

It's a great way to keep your license active without the usual expenses.

If I sense the buyer is cut from this fabric, I will negotiate extra hard against repairs to the extent they simply walk.

The most you'll see is that it comes from some Warehouse Lender, which is usually just another bank or affiliate.