There aren't many multifamilies in the area and the prices vary drastically within a 1 mile radius for properties with a similar square footage. 

If you aren't comfortable with that approach, I recommend partnering with an experienced rehabber.4.

There aren't a lot.

If you read through the posts on subject to in the various threads, you find people who believe subject to takes advantage of sellers, takes advantage of buyers, is unethical because lenders aren’t “informed”, violates some “duty” a borrower owes to a lender, or is flat out illegal.  

I’d recommend trying to get out of your listing agreement or have her step it up because she’s the reason you aren’t selling.

I know many buyers will go with the flow and not object, but I'm especially curious about the experienced investors and people who aren't afraid to rock the boat to save some money.

@Karolina PowellI don't ever do that many at once, but I have noticed recently that title companies just aren't as good about communication in general as they used to be. 

That is for people trained to buy property the correct way, but most people aren't trained so they resort to the aforementioned options. 

Read the HUD guidelines Greg posted, must have seen them for more than one session meaning they aren't going to risk their license to help them and you can call the therapist to verify if you needed to.

Their impression was that most of the short-term rentals operating in the city aren't doing it legally.