My main concern for not renting them separately, and only mentioning that they could rent together is that if I have a group of 10 people and I search on Airbnb, once I input 10 adults in my filters, the listings with 3 or 2 bedrooms that have the capacity of 8 people will not even show up, and I couldn't even know that place can be rented together from the description. 

I did not ask any specific questions about his disability status, but he did provide official documentation proving the lifetime compensation.Should his unemployment be a concern?

Still, at the same time, they refuse to buy my condo, putting me in a very tough situation where I had to foreclose on the apartment to find out later that they picked up the property at the foreclosure court for pennies.If you're concerned about repairs, don't be.

This is a concern that many people have in addition to yourself.

As a fellow investor myself I'd like to give a bit of advise when it comes to condo's specially as to where short term rentals are concerned. 

With inspections costing $400-600, my main concern is that the inspection on the current home goes bad and the same thing happens on the next house.

@Brandon BellDiscuss with your prospective tenants this concern.

The sector is averaging mid to high 4's currently.They don't require income docs, so no dti concerns.

I am surprized now as I am filling a unit now and saying I want to do month to month  because of the current environment none of the prospects so far seem to be concerned about that. 

That is a great question Sneha and a legit concern.