I’ve spent 6 years working in the ski industry in Japan, while I haven’t changed careers I can cover the ski resort side for you.
Working in a resort here is definitely really fun, but it’s a different kind of fun to overseas. I’m not sure where you’re from, but Niseko would come the closest to what most foreigners think of as a ski town with the partying equal to the skiing (Think Whistler, Queenstown, Aspen or St Anton). If you’re at a resort and not a town (i.e. Appi Kogen, Kiroro, Tomamu) the nightlife is quiet to non-existent.
If you want to ski as much as possible, keep in mind that different ski resort jobs will give you different opportunities to ski. “Ride-breaks” seem uncommon for indoors staff at Japanese companies, so if your job isn’t on the snow (instructor, ski patrol etc), you’ll be limited to skiing on your days off unless you work evenings, but at least you get a free lift pass. Your days off are usually randomly distributed over the month, but you can ask in advance if you know you need to go to an interview etc.
At least with a ski job being seasonal, they don’t care about you looking for a new job to start after the season finishes.
If you have any instructing qualifications you should easily find a job at a ski school. You’ll spend all your time on the beginner hill during the busy period (late Dec - Feb), but you’ll have more free time and flexibility later in the season.
Assuming companies go back to in-person interviews once Coronavirus is over, you’ll want to be in Honshu if you’re planning on going to Tokyo for interviews. The snow is better in Hokkaido, but you’ll have to fly (or ferry) to Tokyo. Yuzawa in Niigata wins for accessibility, with a Shinkansen (bullet train) station in the ski resort, but Nozawa Onsen, Myoko Kogen and Appi Kogen are all easy to get to and from by train. There are good overnight bus services from Nagano to Tokyo if your ski-bum salary can’t stretch to a Shinkansen ticket.
Finally, outside the developed resort towns (i.e. Niseko, Hakuba, Furano), you will likely live in staff dormitories. Things have improved but the first two years I was here our dorm only had wifi in the common area and it was painfully slow.
Hope that helps, you’ve got at least a year to think about it!
If you’ve got any questions let me know