Excellent summary, rjc1976!
Blue Mountain (west of NYC on route 78) south of route 80.http://www.skibluemt.com/
(another Pocano ski area?)
My one experience with the Pocanos on a weekend was insane crowds (I didn't even ski).
I'd think that weekdays would be preferrable for -any- ski area (not only Hunter and Windham). Interesting that Belleayre is a good choice for weekends (haven't been there in a long while).
I -have- been to Hunter and Windham on weekends and they have been OK. They -are- much better on weekdays!
Elk Mountain (north of Scranton, PA) is within 2.5 h (maybe) of NYC and nice (I was there a while ago). Montage (-in- Scranton, PA) has got to be reliably insane on weekends.
It would be quite reasonable, if you had two separate days to try Windham on day and Hunter on the other (or Hunter twice).
Of course, Vermont has bigger mountains but you'd need two full days (with lodging) to make that worthwhile.
Of the "local" resorts, the ones in the Catskills (Hunter, Windham, Belleayre) will likely have the most reliable snow conditions (being significantly NW of NYC).
Since you are not skiing much, bring your boots and do a ski demo (rent "high end" skis) rather than bringing your skis. Keep in mind that pickings might be slim at the end of the season (after mid February). Hunter and Windham have on site "demo" centers. And there are a few ski shops out side of both that rent skis and maybe have "demo" programs.