And if we were pressed on mountain places, we’d have been looking at upstate NY, parts of Vermont or western MD/eastern WV alongside the Poconos. We ultimately went with OCMD over the Poconos. How much do you want to use it in the high season(s)? You can wreck your income stream in a hurry.

What’s the legit season look like? Try to get a sense from your agent, look at nearby rentals, etc. What are the property management options? Some areas are easy to pick from a few, some places you have to roll with whatever the local real estate company might be - and you probably have to check with the HOA. How are the amenities? If you can get close (~15 minutes) of a ski area, then the math works better in the winter (and can be fine in the summer), but you need access to something. It can be tough to find properties outside HOAs, although it is possible. How’s the HOA (and what does it cover)? Some Poconos communities border on nutso, some are fine. We did the math on Poconos versus shore, and it depends on a few factors: The fees can also get pretty crazy and cut into your ROI pretty seriously, especially if they are raised unexpectedly in the future (clubhouse needs repairs, putting in a pool, roads, security, etc.). Some of them may be sensitive about rental properties. They’re everywhere, and kind of stand in for the lack of government presence out in the boonies.

One last consideration would be the HOAs. I’m not sure what internet coverage is like these days, but when I lived there ~5 years ago it was lagging behind the rest of the region by a good bit - if you can find a place with fiber or 1gig cable that would be ideal for remote workers. Places that are easy to get to via major highways and within a 10 minute drive to a grocery store and within 30 minutes of urgent care. If you do invest, I would strongly encourage looking at property on a decent sized lake, or very close to public lakes / trails / other recreation, as these are the kind of draws that will keep your place booked up during the summer. Prices have inflated quite a bit from the 2020 rush to live in the woods, and there are a lot more deals to be had in smaller urban centers within striking distance of the NY metro. But as an investment, it’s not where you want to be IMO. If you love the area and want to spend time there for the next few decades, then go for it.

Airbnb in poconos with pool