Thanks @psuhoffman, this is a great reply. My thoughts currently are somewhere between Accident to South near Deep Creek. As you indicate I don't want to be too far from 68 because if it's too much hassle to drive to then it will just become a chore. We do a lot or winter backpacking in places like the Dolly Sods and Otter Creek wildernesses in WV so want to be relatively near those, but at the same time be able to hit places like Swallow Falls in MD.
As you and @nj2va correctly point out it is mostly upslope, my bad, which is fine with me. Those sorts of snows are more reliable than the hopes of a big nor'easter. My wife and I are both originally from Michigan and while we never had costal storms there (obviously) we really miss the array of moderate snows over the course of the winter that really added up. Especially lake effect.
It's a bit of a tradeoff for isolation vs. being near at least some sort of town. We'll need to work on that. I do want some rugged terrain with preferably some hemlock forest (before they're all gone) so somewhere ion the North side of a ridge would be good....but also need to be able to put in a driveway and utilities and it needs to be driveable! Being near Deep Creek lake also wouldn't be bad assuming I could get somewhere that wasn't under threat of immediate development.
I'm retiring at the end of the year so I have all next year to get the land picked out! I'll hit you guys up as I start to circle in on locations as property comes on the market.
Ty