Hey Adam,
This is an interesting question. I can tell you my experience. We wanted to buy a lake house that we could get other people to pay for. We selected an area that had good summer rentals (obviously because it is a lake house), but we also found a lake near a very good football program so we could also get fall rentals. I have found that I haven't been able to fully cover the cost of the house based on our VRBO and AirBnB listing of the property, but it has been close so I just figure my usage, which is about once a month, I am basically paying for.
Here is how I analyzed what I could afford. I used AirBnB and VRBO to approximate what I could get on a nightly rate. I figured that I could get one week long rental and two weekends during peak season, every home game during football season (7 weekends), then about 1 weekend per month in the offseason. This seemed to work out to what we have seen over the last two years. Our occupancy is around 100 days.
We have set up our "Team" with a good cleaning lady and a couple local handy men. This works for us since we are relatively close and we visit the house pretty frequently. In selecting your house, you will want to make sure that house you select has very little maintenance, especially yard work.
I have found that real estate agents really don't understand short term rentals and since we were buying just one property, we really didn't look for a real estate agent with short term rental experience. It was more important that she was available for when we could look at houses and that she would be there for the inspection, appraisal, etc as we were not able to attend.
I would list on both VRBO and AirBnB if you are buying near Hersey. VRBO nets us our longest rentals (week long) and AirBnB fills in the weekends pretty well.
Hope this helps.