There are accountants out there insist that as long as it is a business like arms length transaction that it can be done. 

The roof on this property was over 8 yrs old and the buyers insisted on a new roof with a contractor of their choice (to the tune of $14000 vs $9000).

Personal fave: SF insisting on buying and building “affordable housing” to the tune of $800k to $1 million per unit, for a few lower income (or homeless) people who literally win the lottery and get the unit at a huge subsidized price or rent.

But, he insists to stay

Is it possible that the lender (bank), however, would insist upon an accurate appraisal and inspection of the home and diminish their loan amount, accordingly?

You might suggest to him to switch to a direct-deposit method of sending you rent in order to make sure he never has to worry about it again (you might even sort of insist on that.) 

Still have one unit vacant but I’m pretty insistent on high credit quality tenants and it’s not the best neighborhood for that in the middle of winter.Prop management team is pretty responsive. 

They lend on the same premises that I stated above and they will insist that the loan be to an LLC vice an individual because it makes it much easier for them to foreclose and they are not subject to the new laws governing loans to individuals.Transferring the title after the fact will violate your due on sale clause which is in pretty much every new loan.

I see a lot of advice on these forums insisting on the LLC being the primary named insured.

My HOA, property manager, and the owner of the property below mine insisted the damage was my responsibility.