I have been riding for over 40 years, toured a bit, done most of my mechanic work, and have the basic tools.
In general most mods I have done worked,.. a few failed.
The basement is covered in bike parts since the days of Mafac brakes.
I have built 5 wheels, 1 bike, can tap and mill. Most mods have held up OK.
I thought about frame repair/repaint, but this was what was offered by Trek.
I considered having the shop do things. The shop wanted me to put the stock 28H wheels of this 920 model (discon) on this bike, (and just reading the reviews of the 920, a few people have had problems with 28H rim spoke design). Even with 32H wheels on my bikes I broke spokes. The shop wanted electronic shifters, and hydraulic brakes. It was pretty clear nobody really toured long distances.
I want to enjoy the scenery, have low maintenance and be mechanically fixable out in the field. A few pounds extra will not kill me by going with more conservative stuff. I always carry multi tools.
We learn by reading the forums, bike reviews and talking to other experienced wrench friends and posts like this.
If you roll your own, you will be capable of adjusting/fixing most things out on the road. Your bike will be designed as you need it.
Having that competent knowledge is priceless.