What if they insist on staying but then can't afford it and get behind?

@Ronald Allen Barney I do want to change out of it due to some health issues but if I could do it part time that would be great or for investment purposes.

Raise it slowly, if they complain offer to help them find a more affordable place and find new Tennent's you can vet and know will be able to pay 1500 a month.

My goal is for these homes to be affordable and about 600 square feet.

Add in the risk that Airbnb is the scapegoat for lack of affordable housing, and your business constantly remains in political crosshairs.Then, add in your time.  

In property management you get what you pay for.A good analogy - If you have a health issue are you going with the cheapest doctor available or are you trying to find the best & most experienced specialist in town?

She asked if we would be willing to let her AirBnB the apartment while she is away so she could afford to remain our tenant.

Looking for recommendations for a contractor who could handle this so I can figure out the cost and what I can afford to do with it.

Cash for keys is your best bet, then any kind of health code violations if a municipality cares.

The key is getting the maximum density on the lot for the most affordable price.