Gstaad - A fantastic resort: I have been going there much of my life, and am still enjoying it. Let me list for you a few strengths and weaknesses;
Strengths:
Varied choice of slopes, and if you get bored of the local 250 kms, you can always trip to Diablerets/Villars (40 mins) or Adelboden/Lenk (20 mins) which opens up 400kms more. You will NOT get bored.
You don't ski or board - then you can shop in numerous posh shops, do day trips, gourmet dine, etc.
In the past few years the resort has heavily invested in artificial snow to better piste conditions. This year two new fourpack chairs opened, putting the remaining old lifts into history.
The nightlife may not be as wild as in Austrian resorts, but it has improved significantly over the past few years. One can chose from about 6 very different clubs - of course the special ones (GreenGo, Hush, Chlösterli)in Gstaad itself are pricey.
Weaknesses:
Most of the resorts are relatively low altitude, up to 2200 m.a.s.l, with exception of the Glacier resort. Also, many of the sections are disjointed. This may be annoying at times, but helps protect from annoying day tourists which tend to avoid the smaller resorts.
It can be pricey. A 2dl cocktail in the best clubs will cost you about £15. You can of course avoid these sites. Accomodation is also generally upmarket, but there is a choice of 3* hotels. You can also escape high prices completely by staying in the more quiet Rougement.