I'm going to disagree on the GPS, it is not very high on my list of important gear. It sure is nice to have when navigating a strange city, but I personally would be just as happy not carrying a GPS. I'd just accept that I would spend an extra 1-2 days fumbling around any big city I'm in. On the other hand, it is also useful if your speedometer on the bike does as mine did....
For me, the best thing I've taken so far has been good quality camping gear. I prefer camping to hotels/motels (and not because it saves money, that is just a bonus). What makes camping work so well for me is that I am extremely comfortable, always dry, and camp setup/takedown is very fast. But this requires planning, not just buying whatever is handy and cheap. I use an exped downmat for my pad, a down sleeping bag (Nunatak Arc Alpanist), and Big Agnes Seedhouse SL2 tent.
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