You might want to look at rain chaps. They'll block the wind (and most of the rain), but your legs can breathe out the back.
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It may be the case that you can no longer buy a Shimano square taper crankset, but there are plenty of offerings suitable for touring bikes from the likes of Sugino, Stronglight, IRD, Velo Orange just to name a few.
If there are only one pair of eyelets at the rear dropouts and you need to "double-up" both the rack and fender stays on them, be sure to fit the rack's stays to the inside. That minimizes the cantilevered load on the single M5 bolt.
Are you just looking at a three week tour with nice scenery, mountains, and services? Doing something like the Northern Tier from Anacortes to Glacier National Park would be a good choice, and possible to do without camping if you plan ahead. If you're travelling fast and light, you could do it in three weeks, and then have time to spend at Glacier. You could also catch Amtrak out of Whitefish to get back to where you need to.
I think you will find the LHT ill suited for faster rides rides, unless your definition of a faster ride is relatively slow.
I have front and backs, so maybe I'm ok with space??? Maybe!