Our vacation rental is along the Virginia coast, we get about 9 weeks in the summer, 2 in the spring, and 3 in the fall. Spring and fall are primarily birders and wildlife photographers. In an area like this it will be extremely difficult to cash flow, I haven't met anyone on the island who does (unless they don't have a mortgage). For me this is more about other people helping us build equity. We do cover the mortgage but that's only half of the expenses. Eventually, the property will be self-sustaining. Because Chincoteague attracts mainly families and Birdwatchers, there is not a lot of wear and tear on the property unlike Jersey Shore rentals or other places that attract large groups of college students.
Our property managers are great, they charge 16%. I usually implement every suggestion they make. Because I listen to them they work to keep our house rented as much as possible, more so than my neighbors who tell them their house is fine the way it is. I have friends with vacation rentals in Cooperstown, NY and Marathon in the Florida Keys. The Property Managers in those areas charge 30% - 35% and have significantly high cleaning fees. The property in Marathon Fl. rents for about 30 weeks per year because Northerners go there in the winter and mainland Floridians go there in the summer because it is cooler than the rest of Florida. I've heard that Key West is a good vacation rental market but the upfront investment can be significant.
We live in NY and have several friends who have gone through the 6 -12 month process of evicting people. With VRs you have to be of the mindset that you have Guests, not Tenants. I like that our Guests come for a week or two, pay ahead of time, and leave. I love that our PMs have it cleaned, check in our next Guest and mail us a check.
You can have 50 vacation rentals, I've met someone with 64 VRs. However, if you self-manage, you'll have a job, not an investment.
