This is most likely my reality as well (though 58 seems a bit ambitious for me). And one of the advantages you mentioned definitely resonates with me -- being able to visit lots of different places (which of course, you could still do even if you re-located). I've loved every ski day that I've had, but I've never skied more than 15 days in a season before. Would it be possible for me to get tired of skiing if I did it more frequently? (Silly worry?)
For me, getting tired of skiing simply doesn't happen any more. When I was a working and a "terminal intermediate" skiing groomers on a ski vacation out west every 2-3 years, that's when I could get bored and/or tired enough that I would stop skiing before last chair. First time I skied >15 days as an adult was 2007-08, the first time I took my daughter to meet up with friends and ski Alta for a few days.
For 2014-15, I planned two trips out west with friends who were advanced skiers. Mid-season I skied around SLC for 13 days non-stop, the late season trip ended up 18 days of skiing with a couple days off (1 travel day, 1 too warm so went shopping in SLC instead). Most of those days started close to first chair and lasted until at least until 3pm, longer if conditions were good. When I started skiing more as a retired parent, I was around age 50. That changed after I had to do knee rehab (not a skiing injury) the summer of 2012. I'm in much better shape than ten years ago. Also invested time and money into high level lessons over the last few seasons. Found a small group of ski buddies for trips out west. In short, having worked at becoming a solid advanced skier who can handle a wide variety of terrain and conditions, I never get bored on skis. I even have more fun skiing on short groomers in the mid-Atlantic than before because I know how to use the terrain to practice skills in order to be ready for big mountain skiing.