Waiting until Fall or Winter means you'll have fewer prospective tenants out there looking. 

Fun fact: I did visit Covington briefly while I was in Cincinnati to get a quick feel for the area, and I did see some potential.

I have always wanted to try this but didn't know enough about it to know if it made sense (versus just sounded fun).Have you ever used Airbnb to rent a single room or only whole places?

The posters who make fun of the posters

Another example would be a tenant goes on vacation in the winter and heater breaks and freezes the pipes, because the tenant was on vacation or not home its not their fault.

Any tips you have when dealing with a tenant who consistently breaks lease, lies about property damage / repairs needed, does things like keep the heat off in the winter when shes closed for the one day a week.

Experience or not, we each host a little different, and having the pressure of them looking over everything you do is not fun!

From my experience of owning and operating 3 STR's in San Antonio, the mid term rentals have been great during the late fall and winter months, but you'll definitely want to take advantage of STR during the late spring/ summer here.

In any case, I attach below a screenshoot of the seasonality page for Fresno, CA.You can see that the demand is higher in the summer than in the winter season.

Quote from @Marc Winter: Why bother--just say NO!