Unfortunately, timing was about 2 months late and the market went dormant for larger homes in our area around late August when we had the home finished.

Have you taken the time to search AirBNB and VRBO in those specific areas to see how many STRs are operating?

I’m in a small financial bind right now and I could use the $300 back, especially since I’m not really planning on using the pro features any time soon. 

It’s their full time livelihood to make transactions happen.  

Great tenant that always pays on time - been there for 5 years Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

in a stick frame market and one of the cheapest markets to build we build with margin at $190 or so a square foot. that will go up over time about 5% or 10% a year to keep up with new build price increases. we are buidling a 3 story walk up and source some of the lowest priced crews.

@Michael Baum how many Short-term rentals do you manage this way where you are on call all the time?

At that time we could renovate the ground floor apartment and potentially turn it into (2) apartments for a total of (5).My questions come down to how do we deal with the existing 40k mortgage, whether we can make it work so her parents aren't paying much in rent, if anything at all, and whether or not we set up any legal entity, like a trust to help the legal situation of paying off her sister down the road. 

Amateur investor/full time agent here. 

He gives an example of 123 Main street (total profit/total invested capital)/time in years.