New board member seeking 14er advice

[Tornadoman]

The other issue with the Crestones and KC/Challenger is route finding. Of particular concern is finding the "Avenue" on Kit Carson on the way back from the summit, and the proper point to switch between gullies when descending Crestone Needle (I haven't done the Needle personally). Both of these have led to deaths in recent years. If you do pick those routes make sure to pay a lot of attention to route finding and take frequent looks behind you so you recognize the terrain on the descent.

[Scott P]

is there a 14er that has the best chance of having good weather?

Too early to tell.

I know I am taking a risk flying out for such a short amount of time in early October, but it's totally worth it to feed this new addiction.

It's not that big of a risk since there are plenty of non-14er hikes that can be done in cold weather without that much gear.

[Wish I lived in CO]

I won't have the time or the equipment to hike it overnight.

How much more difficult are the crestones? Is Kit Carson too advanced?

I'm no expert, but guess I've been through a few paces now. Used to live out East and fly in for 14ers like you are doing, so I know that drill well too. The Willow lake area and much of the approach are visually stunning and a big reason that KC is my favorite. 8 years ago KC / Challenger was only my second 14er (attempt) at the time. The Challenger face was too steep for me then - newbie at the time. It gets worse if there is any precipitation / ice. That Challenger face has turned me back 3 times out of 4 now, including just this June on a re-visit with a friend that wanted to try it (lingering snow got us). Can you do it? Sure / Maybe. However, just wait until next year to have much better conditions and a little bit more experience as well. As others have pointed out, anything in the Sawatch, or Humboldt (also very scenic) would be better choices at this point for October.