Lucas, I'm starting to prep for my own epic 3800+ mile ride in May to Sunny CA & back. My requirements overview for comfortable distince riding from lessons learned the past couple of seasons:
+1 on the sheepskin/shearling seat cover (I'm also gonna try a beaded seat cover that may help relieve some fatigue....)
+1 on the wicking briefs-(I tried Rich's cutoff sweats trick after the Midwest rally last year...worked OK @ fending off monkey butt for me for awhile...I think wicking briefs & the shearling seat will work better tho)
+1 on installing a throttle boss/palm rest
+1 on a beverage holder
+1 on ATGATT
+1 on 10min walk around for 2 hrs of riding & fluids/snacks
A windshield is a must!
+1 on a backrest....I use my travel duffle for one and it does help with back support.
I carry some small packets of Paceline Products motorcyclist's "Butt Wax" in my tool bag (This stuff is good to ease discomfort from chafing & windburn)
Motorcyclist's Butt Wax