As long as I do not lose money I think I'll be ok with that.

However, you can't sell something unstable, with circular references, requiring human override, etc.But, if you stabilized it, the model loses efficiency. 

I've heard too many stories of investors purchasing homes for STR use, only to find that they lose their permit or the ability to transfer it when they sell.

Why would I be cash flow negative and losing money for years and years?"

I was losing money every month and was done managing the property.

Most of these folks don't want to lose their voucher.Additional issue, when rent is too high, it slows down leasing. 

Who wins and who loses?

We'll lose money for 75-90 days but the new rent is market so some will stay and not forcing people that can't afford it to move in the middle of a very cold winter I think buys a tiny bit of good will and is the decent thing to do.

The new released estimated total of the effected areas is now in excess of $250 Billion.

I would like to park my license somewhere so I don't lose it.