If he was a "ski bum" I'm guessing he wasn't commuting to Denver, but to get to the mountains up there he'd have to drive the extra distance sometimes.
For me, I just saw it as disposable income. I was making good money at the time and it never really occurred to me it might not be a great deal. I just figured I had $500 more to do what I wanted.
And caveat, I wasn't going every day, A lot of the back and forth was variable depending on weather and conditions. The sad part is you can't either these days thanks to Vail. Also, gas was a LOT cheaper back then - it was hovering around $1.75 if I remember correctly so the math works a little better, but not really ideal.