I thought a 'resort life' is what I wanted growing up. I got a degree in resort management and made a go of it. Ultimately, outside of a few positions that are highly competitive and often take 10-15 years to attain, working the hospitality business doesn't typically satisfy the income needs to support living a comfortable lifestyle in resort towns; the cost of real estate is simply too high. If I had to do it all over, I might have focused my education towards professions that pay a bit better and still have opportunities in resort towns.
I eventually moved 'back to the rat race' and what I found was I actually enjoy living near if not in a decent size metro area more than I did living in the mountains. Two years ago we moved out of downtown Portland, ME to a smaller town. We enjoy it here, but both miss living in a vibrant downtown where we can walk to restaurants, music clubs, parks etc. We'll probably move back to something similar to what we enjoyed in Portland after here.
As much as I love skiing and visiting the mountains, I have no desire to be there full time. I would maybe consider moving back to Burlington, VT, but that's about the closest to 'resort life' I'd consider.
