I ride as often as I can in the driftless region as well. I ride older bikes generally with a triple but end up with low gears similar to what you'd get with a 46/30 or 48/32.
That change makes sense particularly since you have considerable experience riding in the area and you know that the current gearing is not working for you.
Changing out the BB is not difficult and there are youtube videos you can watch. Your call but I'd vote for doing your own work.