Coming from the Worcester area, only Berkshire East is closer than southern VT. Going out to Jiminy is a waste. Been meaning to check out Catamount on the Indy Pass this year but it's no quicker than Loon.
And as you said, theres much better stuff in the Catskills if youre coming from NYC/NJ, so no reason for them to stop in WMA either. I guess Jiminy gets some Albany traffic, but even that doesn't make sense to me given their proximity to southern VT.
skied berkshire east for the first time this year, and with decent snow and everything open i'd much rather ski berkshire east than windham or hunter. indy pass free-ness helps for sure.