Try to make quitting a last resort.

It no longer exists but used to be a resort island in New York.

@Curt Davis ultimate plan is to open a successful resort.

That's not a great way to portray yourself, since you have to deal with other investors and lenders, some of whom may recall that you were looking back in Feb 2016 for a way to get a loan you aren't entitled to, and would resort to false statements to do so.

That said, if you live in a seasonal resort town or everyone in your area is going month-to-month, then that is your answer right there...Read voraciously (real estate books, websites like this one, and all the rental ads in our area, etc).

For a cheaper entry point find a cabin in the Adirondacks somewhere, preferably near water AND ski resorts for year round rental income.

I have several family and friends that run STR in the country side some near and far from mountain resorts.

During this time, visitors come to enjoy skiing and snowboarding at the many resorts in the region, such as Camelback Mountain and Shawnee Mountain.The winter months can be just as profitable as the summer months, with high occupancy rates and premium rental prices.

Are investors really resorting to direct mail / spam / bandits to get decent deals? 

Put up a fence, a big garden, hammocks, give it like a resort feel.