I rarely see anyone address the underlying root cause of the issue.

@Stacie Telles  You may be able to refinance your property if the repairs or remodeling have caused an appreciation in value.

That is where the concern would be for me.Yeah, older tenants may think that it automatically makes someone a criminal of something, but I would just explain the card and that it at least, in theory, has a medical purpose, unlike cigarette smoke which kills the smokers and everyone else around.

I’m wondering what all I need to provide my tenants with this year as far as taxes are concerned.

Typically those purchasing cash aren't inspecting every home, they're walking it or having their go to GC walk it and already know what they see that may be a concern. 

I would limit the open calendar days on VRBO to maybe only 30 or so out so as to not cause any/many issues (having too many dates show as booked) when I subsequently go live on Airbnb.

It wasn’t on the lease, and it was starting to rot, posing a safety hazard.We knew tearing it down would cause an uproar, so instead, I suggested something a bit unconventional.

I have a few commercial bank contacts, but concerned they may just cut me out of the deal.

If they do, you may have a chance under the scenario you're proposing - if they share your concern for it's condition (although that seems unlikely since they've been living with it the way it is for some time, it seems).If you own it, it's pretty lowbrow to expect a neighbor to invest in your property. 

The contract with the wholesaler also expires on Monday the 27th, so I have my concerns about this just being a stall tactic to get out of the contract.