large variety of slopes, interconnected skiing region
too low for consistent snow, not the best apres-ski town
I've spent a week or two for the past ten years in Kitzbühel and that alone should tell you enough about the quality of this ski resort. Nowadays I'm in my early 30's and I have always come here with my wife who enjoys the region as much as I do.
There are a couple of important attributes to this town and its surrounding skiing region which I'll explain in more detail:
_ Site/Geographical situation _: Kitzbühel lies in the western part of Austria in the state of Tyrol in amidst the Kitzbühel Alps, which are a mountain region surrounding the town. This allows for skiing slopes on entirely different mountains and terrains with a number of different starting points to take you skiing. The only drawback from Kitzbühel's location is the low altitude of below 800 meter (2500 feet) which won't always allow you to use slopes going all the way down into the valley. If I had to quantify this limitation, I'd say the best chance for having enough snow is from the months of January to March out of a likely season starting in December and ending in April.
_ Travel _: it's rather close to three international airports (100km to Innsbruck, 80km to Salzburg and 120km to Munich) and it shouldn't be much longer than one hour to both the Italian and German border. Although the town is out of its way of the regular west-east train route (Innsbruck-Wörgl-Salzburg-Linz-Vienna), there are still several daily EC and IC trains available.
_ Town/Infrastructure _: one could almost miss the going ons in Kitzbühel and label it misleadingly as a "sleepy mountain village" and that may even be true for short amounts of time when its townfolk aren't outnumbered by vast amounts of tourists. The rather small town with about 8k townfolk offer almost 10k beds in its immediate vicinity, not counted more than 1k secondary residences. The town rather caters toward the older crowd which is manifested by a number of celebrities owning homes here, making the area feel a bit like a luxury vacation place. There are a number of important events that draw people to the area, at winter time the most notable one is the Hahnenkammrennen, one of the most prestigious downhill races in the fis world cup. If you want to meet tens of thousands people, then the third week of January would be ideal for a skiing holiday. During the Hahnenkammrennen-weekend you'll lose a few slopes that lead almost into the town, but the rest of the region is still open to you. Finally, if you're not too tired after skiing or if half a day is enough for you and you want to experience other things, then you'll have plenty chances as long as you're interested in sports or sportive events. For anything else, you aren't too far away for doing daytime trips. One such example is shopping - while the town has some nice boutiques, anyone looking for a "real" shopping trip will need to go 40-100km to Wörgl or Innsbruck.
_ Nightlife :_ there are a number of night clubs and other establishments available, but Kitzbühel could never be compared to Ischgl or St. Anton in that regard. If you're looking for aprés ski or if hooking up is an integral part of your vacation, then you're on the wrong track here and should better look for a region that caters toward younger crowds and party people.
As an ending note: after ten years of coming to Kitzbühel I haven't grown tired of the downhill terrain and its many different slopes. If you can live with a few caveats and don't have too high an expectation of anything that happens outside of the skiing part, you might like it as much as we do.