I've been a full time instructor for over 30 years so I'm not totally unaware of how it works. I am considered a ski bum by others 'though not myself.
Step #1 Know yourself. Ok, You've got a start on that. But why do you want to be a ski bum? I wanted to ski enough to put up with the rest of the nonsense around it. Over time you will find out more about what works for you and will adjust. Thus...
Step #2: Be Flexible. Figure out a plan, but don't be thrown because it won't work. Look into any and every job, and living arrangement. Dishwasher is a popular route with a lot to recommend it. I started off as a contract draftsman. It let me pick time, place, and to a certain extent pay, to get me through the first couple years.
Step #3: Be Early. Good jobs go fast, Good housing goes Faster.
Step #4. Marry Well. The first three steps are easier single, but living is easier when married to someone who also wants to be a "lifestyle bum". If your spouse brings assets like cash or health insurance great, but unless you both want to spend your life engaged in your life rather then pursuing "success" it's a long tough haul.
Step #5. That includes geographically. For me, I found that resort town living was not my thing. I wound up in Montpelier VT. Not a traditional ski bum destination but closer to more skiing then most western towns (45 minutes to Sugarbush, Stowe, and Mad River Glen) as well as more non-skiing/tourist based jobs.
Step #6. Find a summer job that you also love, or at least like. In all likely-hood your summer job will pay the bills, the ski job will be financially treading water.