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I would post the final route the morning of the ride after checking weather and official closure information. Conditions change faster than old forum posts.

A low-range tire gauge that is easy to read. I use it every ride, which is more than I can say for half my sockets.

Trying suits for the first time. The best candidate pulls at my shoulders when upright but settles into place in a tuck. How uncomfortable is too uncomfortable before break-in?

Before buying anything, make sure the foam plugs are actually inserted fully. Rolling them thin and holding them while they expand changed everything.