Justin: "There have been times where I really wished that I could work 10 days straight and have 4 days off... but that would never happen."
I know lots of people who work "2-on, 2-off" which means 14 12-hour days (they feed and house you) and then you get two weeks off. THIRTEEN TIMES A YEAR! Now, if you drive truck, weld, or operate oilfield equipment, you might also be earning $90,000-$130,000 in those North Slope oilfield positions. But if you can get by on $40,000-$60,000 then house keeping, office work and food service is an option, too.
A budget could look like:
$50,000 annual income.
Change your address to Mom & Dad's house (saves $20,000 rent right there).
13 round trips to Anchorage (where you report for work): $7,000
No food bill for half the time.
Those 13 round trips don't all have to be back to M&D's - might as well go someplace fun / outdoorsy.
Some of the 13 shifts (May-September) are obvious times to stay in Alaska and recreate here. Heck, don't even fly back to Anchorage - the Brooks Range and Gates of the Arctic would be on your doorstep.