Highlands is kind of a big ridge - there are really long steep expert trails off each side - Steeplechase comes to mind and I forget the other side but we did em. I never got to HB but that is supposed to be a classic high alpine bowl (steeps, pow etc). The mountain skis 3000+ vertical. There are runs where you can look down 1000+ vertical feet and wonder if you fall if you'd keep going
: I really liked Highlands, second only to Snowmass.
Snowmass has over 4000 VF and is the largest - probably a little less amount of expert terrain percentage-wise, but it still has a lot because it's so big. There are cliffs and such there too. At the top there's a rope tow where we skied a gentle snowfield with fresh pow each day. This is at over 12000 feet. Also off the top is a bowl and some chutes (Cirque Headwall). There's hanging valley wall area, which as I remember is really a cliff in places, and people do jump off (not me if I have a choice, chutes are about as crazy as I get
. There's a wide variety of terrain and more than a few distinct areas - the Burn is nice, kind of rolling upper intermediate trails near the tree line. There's a lot of groomed near the bottom (say the bottom 2K vertical - as much as most resorts).
Ajax has a high percentage of expert terrain and moguls (much less groomed than say Snowmass). Kind of like Highlands with ridges and steep trails. It's probably the best setting of all of them - you can ski right down to the town of Aspen and multimillion dollar condos and such.
One thing that I saw when in Aspen is just how different the weather can be top to bottom because of the vertical. It was spring when we went - late March. We saw some freezing rain near the bottom one day which turned to snow further up. This was most drastic at Snowmass as it was really warm at the bottom, with peanut butter slush and fresh pow in that field at the top and a thunder storm in the middle at one point - great to ski through the seasons on a single run