Originally Posted by saddlesores

if you've been riding the bike for two seasons, then you're the expert.
how has the bike held up and performed for you so far?

of course you've loaded up the bike and done a short tour, so what were your concerns?
(aside from the wheelset, which is a given.)
did you load it up with rear panniers, or as a 4-bagger, or bike-a-packing style?
how much weight did you carry, and what sort of terrain did you cover over your test tours?
are those conditions similar to what you intend to ride in the future?

Originally Posted by djb

if you get a new wheelset, make sure that you ride on those wheels for a while, and then get a good wheel building mechanic to go over the spoke tensions and get them as perfect as they can be, uniform tensions--before you go on this trip.
Don't get this done right before the trip also, so you can put a good amount of miles of loaded riding on the wheels to make sure there are no issues.

this is always a good idea before a trip, especially if you are going to be in more remote areas.
Also if in remote areas, I would also recommend getting a spare rear derailleur hanger, in case you ding your bike and bend the replaceable aluminum hanger.-- this does happen.
Last summer I was on a short bikepacking trip in Scotland and met a guy in a campground who had done just that. He had been riding on the sameish route I was on, which had a fair amount of single track and stuff to smack your rear derailleur on if not careful. He was lucky to be able to ride to a bike store where they actually had a spare hanger for his bike, he was very very lucky.

re your headset--if the headset is well greased and properly adjusted, especially with wider tires at appropriate pressures, don't see why you would have an issue. I have bikes that when adjusted properly, go years and years with no headset issues, and really I haven't had a headset issue for about 30 years on various bikes.

final thought, look into doing a bike mechanic course if available, it is so useful to be more familiar with your bike and knowing for sure how things are, especially if going off the beaten track.