Preamble:

Howdy! I currently own a rental property in Boston which I house hacked and am actively trying to acquire another to do the same. However, the market in my area is very hot, and I haven't been able to find/win anything that works, so I'm looking to expand my strategy which brings me to this question.

My family owned a cabin in Newfane for many years but had to sell it a last year. I love the area and miss having a place to stay when I visit, but I don't want to make a poor investment based on nostalgia and wishful thinking. I am investigating whether I could make a viable business out of a vacation rental in that area, perhaps Dummerston, Newfane, Marlboro, etc. I would use it maybe 14 days per year, and it would be available for rent the rest of the time (ski lodging in the winter, woodsy get-away in the summer, leaf peeping in the fall!).

I would need to hire a local management company (or, at least, a local on retainer to be available to deal with issues). I would also need a local cleaner between rentals (possibly the same person). In a emergency, I could be up there in 2 ½ hours.

Taking into account comps from other rentals on VRBO & AirBnB, services fees, VT room tax, cleaning and management costs, I think my break-even would be in the 60-80 nights/year range. I am looking in the $175K-$250K range.

Questions:

• I've listened to Podcast 229 with Zeona McIntyre and read the articles about short-stay on this site. What other resources might I have missed? Any good books?
• Has anyone done this before and what am I not considering?
• Is remote management too much of a headache? Will the costs eat me alive?
• Is there enough demand in this area to think that 60-80 nights is reasonable?

Thanks in advance for any help or insight you can provide!