The whole outfit is heavier than need be. I would take a very close look at packs and sleeping gear, at your electronics, and at your clothing. All are, in my opinion, overly heavy. Incidentally, your stuff bag weighs very little so wouldn't worry about that, but I save on space and stuff time on my down by just putting my sleeping bag loose in the bottom of my pack (but inside the trash bag liner...and watch the liner for holes).

Yeah, the pillow can certainly go. When I have no clothes left in the bag, I use leaves. Works fine.

I used just a 40 degree (F) bag (second one was Western Mountaineering, one pound) right through Maine in September, both trips, but slept in every piece of clothes and with a bivy (second time bivy was very light). It shouldn't be much colder when you start.

I think you should add pymethrin for your outer clothes (or soak them ahead of time).

I've gone nobo both times, but have met about half a dozen folks who started sobo and flipped. They all gave me the same three reasons for flipping. Those reasons were:

Delayed start. The rangers are very conservative in deciding when it's safe to climb Khatadin.

Bugs. As I understand it, you get down off the mountain right into the black fly/mosquito bloom most years.

Water. The northern end of the trail tends to be very wet even in fall. I'm told that most years in spring the wet spots can be knee deep and the trail hard to follow, with some log bridges and wooden walkways submerged.

I'm hoping BianLe will respond. He's done it sobo and went all the way through. He'll actually know the northern end in spring, rather than just hearing about it like me.

best, jcp