I did the 'ski bumming' thing for 15 years,(learned at 25 yrsold) before giving it up at 39 years old. I skied on averege 100 days a season for 15 years.. I'm now lucky toget 5days a season in. Website like this and watching ski movies helps me get the fix.
You do what you want to do. Be it a lawyer or a ski bum. Do what makes you happy, what your enjoy. Don't let the norm tell you what you have to do , be this do that,etc.
I made alright money in 15 winters, summers were somewhat tough, hard to find a employer that would only hire(non constructtion trade) 6 months. and none would buy you a season's pass. I was lucky with a couple of summer jobs, that let me cut y hrs down to 2 nights aweek /on call.
I do not regret those great years. the job i have now takes me all over the USA. I wouldn't be able to be stuck behind a desk on the 60th floor with no windows to look out.
And yes i do carry the ski gear in my truck, so if by chance i can get lucky and lay over near a resort.
Even today i have still have life long contacts in the industry, that will hook me up when i want to make turns. You will b surprised what a 12 pack of beer will get you
You say your girlfriend is a flight attendant. I say marry that women now, so you can get the family flights benies,,, then you can fly to to where you want to go skiing.