Time and again I ask myself this same question...
Let me explain, since starting to ski, a loong time ago, for day trips, me and my family have always roamed the various ski resort of the Italian Alps (and places in Switzerland like the Engadin Valley) that could be reached with a 2-3 hrs travel (either bus or car)
This allowed us to get to know different resorts and see lots of places. And, to some extent, was keeping "boredom" away.
But this had a series of drawbacks, amongst which our knowledge of the areas was limited to, forcefully if we were skiing "alone" (e.g. without mountain guides), to the signed trails and to a little bit of sidecountry. The other is that we were compelled to leave our village early and come back late, and this in turn meant for the major part day trips only (with the occasional week end and the traditional weekly skiing holyday, in mid winter).
Not only, another aspect that we were missing was what I would call "socialize", that is, get to know locals and become one.
an aspect not to underrate...
On the other hand, choosing to go to ski (and maybe rent a flat for the season or buy it) year after year, season after season, to the same mountain was allowing to expand from the marked trails to the whole mountain, get to know other people, and thus more opportunities. But it could become boring, after a while, or not?
In late years, while still a bit of a gypsy, I've chosen to go to ski for the most part to the same mountain, and so it has happened that now I can recognize who is local at that mountain, and who's not.
I have started to expand ,as said, from "marked" trails mostly, to "whole mountain" (whenever possible), this also thanks to the friends I've made there.
So, when you think of it, who are you? A "gypsy", or a sedentary? Of course no one is completely one or the other...
Which other aspect of this have you thought of?