Hopefully someone will answer this better than I because this will be somewhat convoluted...
I drove hwy 50 about 16 years ago and I do not recall very many hills...but again, 16 years ago.
Hwy 24, uh, yeah, I rode my road bike from Vail to Leadville and it seemed somewhat mountainous but again, a much different perspective. But keep in mind, Leadville is at 10k feet so there has to be ascents.
I take Hwy 285 from where I live and then to Buena Vista and up over Cottonwood. Yes it is a pass, but there are far worse passes in CO than Cottonwood where I would not consider towing my TT. Cottonwood? That would be my only choice as going down to Gunnison adds a good solid extra hour. Plus the drive is not as scenic.
EDIT: I see, you're talking hwy 24 from Co Springs area. Completely different part of hwy 24 however I have driven that stretch. Again, a while back but if you are looking to avoid Cottonwood Pass, probably take 50 to Gunnison.
