I am in the Poconos and I do vacation rentals here.
1) Anyone have experience with Pocono vacation rentals? What type of occupancy have you seen?
It's mostly people from nearby cities, for a "boring" house most likely you'll get 6 very busy months and 6 "pays the bill and a little bit extra" months. And if you make it very unique you can get a very busy 12 month period.
2) Is the idea of running a vacation home from afar (about 2 hour drive) nuts? (Vacation rentals are really possible where we live).
You will need cleaner and handy person times 2, or 3. The most stressful and expensive will be the cleaner. If he/she gets sick in the morning and didn't want to go clean that day, do you have back up?
If you are 2 hours away, it is not fun to deal with this. In your situation, you will need a cleaner who can wash your linens as well and that’ll be extra. Expect the first few months to really test the water.
Expect 30% of your gross to go to cleaner/handy person, per house. There are some management companies out here that will take a percentage of the gross and “manages” it for you, but cleaning is extra.
So if you can take care of this [plus a handy person to call when things break], you can do this remotely.
I had people who "cleaned" for me but in fact, never did, except to just change the linens. As you can imagine, I got a lot of dings on "cleanliness" review. So it doesn't hurt to call the 2nd cleaner to go in once in a while to do a check up.
3) Our website is run under an LLC and is profitable. Could the LLC buy the property?
If you have an out of state LLC, I think you can buy it, but I am not lawyer. I would think it make sense to make a new LLC in PA and buy local.
Insurance is about the same for rental [LLC] or individual around here.
One last point, there are some small towns here that banned Airbnb outright. A few towns that tried lost the case in PA state court.
Mt Poconos and Stroudsburg are 2 that were lost such cases to ban Airbnb. So when you buy, make sure you ask or read the town’s ordinances. If it sounded not very Airbnb friendly, than it’s risky. The towns that already lost the case against home owners are safer bets.