I generally have found not pushing to be easier, but my bike has nice low gearing, so hopefully yours does also. That said, sometimes a short walk up a hill can feel good because different muscles are used, you just dont want to whack your shin on the pedal, which can happen.

re riding comfort, there is no magic answer here, and why its better to have ridden your bike a lot before going on tour, to get little details dialed in. Often just a small change of this or that makes all the difference, and riding a rather heavy bike, like 80-90lbs or whatever yours is, means that little things will show up discomfort.
Same with knowing that your padded bike shorts work for you, or whatever.
The more you ride though, hopefully the better you get at noticing perhaps small changes that can make a difference.

all the best