happy Up 2.0 user...
I have had one for a little over a month now. I hesitated because of the disastrous first gen release. Out of all the devices the Up is the only one I would not be embarrassed to wear. It is a lot less clunky looking and "almost" looks like an odd piece of jewelry, but slim enough to shove under your shirt cuff. Syncing manually is a non-issue, and no painless (takes seconds). I usually sync 1-3 times a day. Battery life is about 10 days fully charged. I wanted something to force me to move more and be more active, and it is working. I love the sleep tracking, even if the numbers are occasionally depressing. The smart alarm is one of my favorite features, and the power nap one is great as well. I haven't bothered to delve into the food tracking yet, as that was not was I was looking for.
I am not upset by the lack of wireless syncing. Bluetooth is buggy, and a battery eater. Zero issues with the cap, it fits snugly. I do not shower with it, other than that I am wearing it. I always have my phone with me, so it is no big deal to sync on the fly if I want a status update. No regrets, it was a great buy for me.