If they don't pay or violate the lease in any way, they can lose their vouchers. 

He said abusive Section 8 tennents can be reported and can even lose their Section 8 eligibility. 

Either1) your startup takes off and you can distribute profit fast enough to pay off your debts, or2) you find another source of $100,000 a year (which barely even starts to pay down the $300k, but might provide a better chance for a better loan), or3) you BK and possibly lose the rental houses to creditors (hopefully not, but we don’t know how they are held), or 4) you sell the houses, take the tax hit, work with the IRS on a payment plan whose interest will be much lower than your CCs, and focus on the startup.  

It depends on if you want to make money or lose it. 

Do not be surprised if you lose your entire investment and maybe more, if you have a recourse loan.On the other hand, real estate is a forgiving asset class.  

You'll probably lose a little, but at least you'll be done with them and can start fresh.

I am very aware of the fact that it is overall a losing game, but I have to work on my psychology on this.  

If you listen to David Greene, he's hearing more and more stories about syndications struggling to keep up with their promises and a lot of investors are losing money, or pouring more money into the syndication to try and save their original money.

As your equity grows, you start losing money. 

Regardless of what you do the senior will likely lose their low rent situation whether you buy the property or not.