At any rate it is possible, but depending on your appraisal it could be a gamble

Anything else is luck and relying on luck is gambling. 

The gamble is that the outcome hinges upon the courts discretion and it’s rare to see specific performance unless buyer can demonstrate that monetary damages aren’t enough to make them whole.

this is only a good idea if you have reason to believe that the area will be appreciating quickly, which is called speculation and akin to gambling not investing. me personally, I would rather put my money on black than bank on market appreciation. negative cash flow rentals are a time suck and money suck.

I was thinking of starting a rent increase for my 1 bedroom tenant voucher due it being low and well under fair market value(Based on  hud and zip code) but my tenant is in the process of having a caretaker for her disability and getting approved for a two bedroom voucher.

That's pretty fair.

I have a city rowhouse with a 20' sidewalk and 5' wide steps with 9 treads and two 7'x7' landings. It's a 4 family, I just don't want that kind of transactional relationship with any tenants. At another property with ...

From a tax standpoint, there are additional disclosures to make when selling a business asset for less than fair market value to a related third party. 

I do have a fairly high percentage of my net worth (35%) in the PPR fund. 

Section 8 vouchers pay up to fair market rent.