Re headset tightness, a mechanic I trust was going over my bike wheels before a trip, checked out everything quickly and recommended I tighten the headset a smidge, I have lots of spacers, he suggested tight until you can't twist the spacers anymore. Said that for cartridge bearings and touring, that tight is better. I had adjusted it just a bit looser than he suggested, but still with no play with rocking.

just thought I'd mention this, I've ridden toured a lot on this bike like this, and it appears fine, no stiffness etc