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Yeah - mine packs down into the pint glass on my desk. I just tested it!
Those NeoAir pads must be great to sleep on, but the faff of inflation / deflation puts me off. On IPWR I had my cut-in-half blue foam pad, which I really like, but the fast riders didn't seem to bother with anything - just rode until more tired. They mostly seemed to try to sleep inside (toilet floors, shower blocks, etc) rather than camp in the bush, for warmth and in case of rain. A lot of the slower / less experienced riders took inflatable mats. I'm generalising, but that was my impression from talking to people and looking at kit lists.
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I didn't really find it much of a faff to be honest. Maybe 10 lungfuls of air without really trying and push it inflated into the bivvy. Then undo the valve while laying on it, slide it out, roll it squeezing out the air, then roll it again and into bag. It's all done while sitting in the bivvy. Then roll up the bivvy. It made such a difference I'm seriously tempted to take one on TABR even after doing TCR with no sleep pad.
I'm the same - I tend to prefer urban sleeps - Welsh towns seem to have a nice bus stop to use and quite a few have large public toilet blocks, though I didn't actually make use of any of them.
Yeah, I'm torn. Having ridden TCR without one I know it's possible but TCR had a lot more options for hotel sleeps than back country USA will.
You're skinny enough that you need a down jacket. I seem to carry mine everywhere and only use it for sleeping in and the 10min it takes to get warm afterwards. I guess if I have a mechanical up a mountain it could be useful. That's why I never sent it home on the TCR even though I barely touched it.
Mine is a crazy expensive PHD jacket - full jacket, not vest so it's probably much warmer than yours. I pack it into a 2L S2S dry bag. I could probably force it into a 1L bag but I'm loathe to damage my most ridiculously expensive useless item :)
I've got a superlight, breathable, bug net bivvy for TABR because it's typical hot, steamy and there's lots of bugs. In the mountains I will have to use hotels/motels or nap and move on before I freeze to death.
I want to get a full size NeoAir pad - I have the Small (3/4) one and it's great but I'd love to have my legs lifted off the ground too. So I think I might sell my old 3/4 Thermarest and the NeoAir 3/4 and get a fullsize. Whether or not I take it on TABR I'm not sure - I'm erring on the side of no, but it would make my bivvy sleeps much better.