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I used a setup similar to that ww paddling. Bottle went through hell, but never came loose. I currently have a military canteen/case on my saddle. I have three of the canteens I use for work, so they're easily swapped, but I have to do it myself.

I used to get the sustained motion from whitewater paddling, but I found it pleasant. A little bit of lingering fun before I fell asleep.

I'm a champion sleeper. It's what I do best. Any time, anywhere, I'm down for a good nap. Everyone's different, but getting lost in some chill music puts me to sleep pretty quick. edit: Something like this... https://somafm.com/deepspaceone/

Are rubber trees rubbery?

For a more macro look, you might want to go cheap to start, and get an idea of what you like. Whatever you get will probably be wrong, so you might as well spend a little money before you spend a lot. If there's 10 different devices, you have a 1 in 10 chance of getting the one that's "perfect"...

If I were to buy one, I like the way the Chester looks. Has multiple loops to choose from.

I've been using a cheap chest harness Jonny made me, and it works great. It's unobtrusive enough I've forgotten it, and worn it home without realizing it.

The idea is it creates friction in descent mode which takes stress off the hitch and allows it to move more smoothly. Keeps the hitch from locking up tight. Friction added in ascent mode is negligible.