If you see a loss in profit because of it, don't take it.

This is not a deal of any kind for you.....you need to gracefully back out, like "sorry man, I can't get involved in something like that" sounds like he's wanting you to write a $50,000 check for his loss.

The tenant could also be judgment proof and trash your place and you incur additional rent losses and damage.

if its commercial prop, why are they at a loss not profit?!

One family even told me they were having money problems after the birth of a child and the loss of a job. 

It wasn't an expensive class to begin with, so I figured it wasn't a huge loss if it sucked.

In fact, I still have a carry forward loss of somewhere around 100k on the books. 

You suddenly will realize that on papers you might be at no loss, but commissions (6% realtors fee) and blah blah type expenses will increase your loss or eat up your profit .

I'd like to sell my home and get something smaller, and then use the savings from the decreased mortgage to put towards investing, but that doesn't seem likely without a considerable loss.

Worse, what about unexpected personal losses not even related to real estate (job loss, health issues, catastrophic event, etc.)?