I had to look up Windham's stats as I am not familiar with the area. Why is this place so expensive?
As with real estate, location is a key factor combined with the type of neighborhood someone wants to live in. For a ski resort, the question is where do most people live who are interested in the amenities (or lack of lines) available.
Windham is in the NY Catskills, which draws mostly from New York City and New Jersey. It's one of three ski areas/resorts that are pretty close together. The other two that are open 7-days a week are Belleayre and Hunter. Belleayre is owned and operated by ORDA, which is p art of NY State government (long story how that happened). Belleayre had no slopeside lodging and not really that much lodging nearby. Hunter is owned by Vail Resorts and is a ski resort with slopeside lodging but not too much in terms of non-skiing activities.
Windham is pretty easy to reach from the NY Thruway, with no mountain driving. There is plenty of nice lodging available for a price. There is an indoor waterpark. There is a very good ski school. There is a well stocked demo hut at the base. There are families who own houses or condos, and probably some seasonal rentals available. Windham in an independent resort that recently joined Ikon. You don't hear complaints about operations at Windham.
Until Windham joined Ikon a few years ago, it wasn't that well known. It's had it's ups and downs over the last few decades. Like Jiminy Peak in western MA and Waterville Valley in NH, most of the regulars at these independent ski resorts don't have much reason to go elsewhere and have little interest in online ski forums. All three have relatively high day ticket prices. Jiminy Peak's early bird season pass is $936. Waterville Valley's unlimited pass is $1036. Locals and regulars get their money's worth from season passes. These are moderate size mountains with at least one high-speed detachable that make it easy to get in a lot of runs midweek or first thing in the morning on weekends. Windham has 285 skiable acres, Jiminy Peak has 170 skiable acres, Waterville Valley has 265 skiable acres. Pretty sure all three have well over 90% coverage for snowmaking since what little tree terrain exists isn't that skiable for very many days.
Does that help put Windham's pass price in context?
I checked out Windham last season for a midweek morning using Ikon. It was on my way to Plattekill, which is an independent ski area in the same region, but is only open Fri-Sun. While I'd much rather ski Plattekill on a weekend, I can understand why families would much rather do the shorter drive and stay at Windham. Since Windham has multiple peaks, probably not too hard to avoid lift lines for an advanced skier. I liked the terrain variety. I would go back to Windham or Belleayre over Hunter.