We need to meet up and compare notes! I started a ~2000sqft addition this fall and so far things are progressing. Rough electrical/plumbing is in, hvac starting this month. Having issues with framer but rest of the subs so far are decent, and have actually shown up! I've been fortunate that a local in my cove has put me in contact with several people, who probably would have never answered the phone if it wasn't for him.
I agree with everything that has been posted. My recommendation would be to rent a condo/house in all the locations mentioned, both during winter and summer. We rented a couple of places in Western MD before deciding to look for real estate. Drive the roads, figure out how easy it is to get around. Resort areas are filled with rentals, and renters are usually loud and obnoxious. Our priority was lake access, walkable roads, and low amount of nearby rentals.
Snowshoe has the best elevation, largest skiing, but outside the resort area is pretty isolated. Not sure what you can do there other than hiking during summer.
Canaan/Timberline are probably second in terms of skiing, and do have Davis/Thomas close by with restaurants/things to do.
Deep Creek is true four seasons with the lake activities in the summer. Even if you buy a place not near the lake, the state park has beach access and a boat ramp. There is a mix of dining options from pub/bar to white table cloth fine dining. Wisp is an okay resort. Definitely geared towards beginners. Timberline is 60 minutes away for more vertical / better snowmaking. We have passes to Wisp but drove to Timberline last year because I was fed up with the broken infrastructure at Wisp (Snowmaking system is old, water pipes were breaking all winter).
What RIC_WX said is probably true in any of the resort areas right now. Most contractors are busy building 15 bedroom, indoor swimming pool, mega rental properties. Do your homework and don't overpay. Real estate in these areas went sky high during covid... Things are sitting on market longer but I haven't seen much reduction in pricing, yet. You are still competing with investors buying land/properties with the sole intent to maximize rental value. My gut says at some point the rental market will saturate and values will correct downward, but who knows when or if that will ever happen.