I did the CT in 2015 (July into August).
I generally agree with Dave S.’s views, except:
I used my headnet ALL the time — you’ll miss mosquito season, but the CT has all these biting flies. Tons of them. Maybe ol’ Dave just wasn’t tasty…but maybe you will be.
I actually wished that I had brought an umbrella. SO many days where the rain would be on/off, on/off, on/off. I got horribly sick of putting on/taking off my rain jacket every 15 minutes.
I did about the same pace as you’re planning, happily used a 700ml pot (cooked 1/day, cold coffee in the AM), enjoyed lots of nearo/zeros, and resupplied on a similar schedule to yours (which worked very well, although I didn’t have someone to come resupply me — I had to hitch into towns). For extra trail calories, I carried potato chips (crunchy! salty!).
I second the suggestion that you go to Fairplay from Kenosha Pass instead of Jefferson (there’s NOTHING there). And the Bivvy is good, but I preferred the Fireside Inn in Breck (loaner clothes, Nicki does your laundry and cooks you a great big breakfast, right in the middle of town).
And finally, if you’re only going to do ONE 14’er, I’d make it San Luis Peak…it’s easy from the trail, and it’s a hard one (long approach) for a day hike…so it’s much less crowded than most 14’ers.
In 2015 I took the Eastern Collegiate option, but went back in 2017 for the Collegiate Loop. West side RULES! All the beauty of the San Juans without the ATVs and dirt bikes…but it is definitely tougher than the east side. You’re gonna walk a lot of talus.
I’m sure you’ll enjoy it. Don’t overstress about gear. It’s more a mental challenge than anything, really. You have to pack the right attitude and roll with the punches – far more important that what gear you have!