My wife and I owned two vacation properties up in the mountains for 12 years. We rented them as both vacation rentals and long term rentals. One of them was a long term rental for several years, the other was mainly a vacation rental.
We know what it’s like to deal with vacationers, tenants, house cleaners, contractors, handymen, and vacation rental companies. It’s not easy.
On top of all that you have to deal with maintenance, neighbors, property taxes, etc. etc.
It can be very challenging especially if your property does not age well.
With that said, in my opinion you need to hit on the hot buttons of the mental and financial costs of maintaining a vacation home or second home without sounding like a jerk.
I suggest you write a letter similar to the first letter on this vacant home prospecting letter page or model the one below.