I work remotely, and granted I have an apartment in Bozeman so have no need to be a true ski bum, i have done several month long trips while working- including living in a tent in Hawaii for 6 weeks and living in my subaru for weeks at a time in MT. Several of my coworkers work from their camper in the Stevens Pass parking lot and ski at lunch/nights. Here are my .02 to all your points:
1) Like others have said, unless you have skills in Computers, Accounting, etc, finding a remote job is becoming increasingly more difficult. Many tech companies where friends work have mandated return to office- or at least some sort of hybrid work. Thankfully, the company im at hired so many remote people during covid, theres no way they can enforce a return to office. All non-software engineers are required to go into the office at least a couple days per week. I would suggest looking for a remote job such as customer support for a big, around the clock company (verizon, apple, banks, insurance companies, etc).
2) No to the Apple Vision Pro unless thats really your thing. When I went to Hawaii, work sent me one of
these bad boys- very thin, slides in right next to my laptop in my work bag. Just one usb-c cable that connects the laptop and gives the monitor power and display.
3) Not too much to say here, foods food. Dont go out. Eat cheap and healthy. Eggs, rice, fruit, meat, veggies. Buy in bulk. I eat 3000+ calories per day at around $40/week. Smoothie with whole milk + oats + peanut butter + fruit, then 3 eggs- 1000 calories for like 2 bucks.
4) There are lots of places that have "Digital Nomad Clubhouses" that are pretty much long term hostels. Look on Facebook, AirBnB, or the local climbing gym bulletin board. You generally end up paying around 4-800/month for your own room cohabitating a house with like 8-15 other like minded people. A lot of month to month leases too, so you are free to travel.
If I were you, I would pick somewhere to live more a longer period of time- like 4-6 months. Forget the remote work, and just find a seasonal/temp job. Both of these gives you more opprotunities to make friends and root yourself a little more. If you move around a lot, you dont really make many meaningful friendships since you know youre leaving soon.
The good news about expensive ski towns is that they always need workers. Find some roommates, find a job working nights at as a bartender/server, have a fun 6 months, then reevaluate.