I don't see how you win the argument and you're liable to piss off what otherwise is a "good tenant".

They eventually came around and we negotiated no prepayment penalty for the borrower so that was a win.

The answer to those two unknown and unknowable questions is what will determine if selling is a good idea, but under most long term scenarios where you are in a strong market and sound financial position with your property, holding has tended to win the day over selling. 

However, if your house hack reduced your housing costs from $1,200 to $600 per month, would that not be a win?

Persist and you will win.  

You can also buy one lottery ticket and win hundreds of millions of dollars. 

Everyone is gaga over LVP but for older homes with rough sub floor site finished HW may win because you don't need as much prep and it will be more durable.  

The tenant has a reasonable chance to win on the appeal do to your mistake with the date.  

Sometimes you will win, and sometimes you will learn!

I wrote him a letter explaining why I need the things I have requested and letting him know that I want to reach a win-win solution for both parties and he is back at the table.