A few more thoughts.
- having built up your bike is a big advatage, you have mechanical skills, but more importantly, you have the ability to know if all is well with your bike, and to recognize any slight problems before it gets to the broken down stage.
example, on a 6 week trip, on a rest day, doing my bike clean, oil chain, inspection routine, I noticed the front hub cones had some play in them. (First for me on a trip) so being in a large town I found a bike store and the owner whipped out his cone wrenches and put it right.
Someone who never works on hubs would never have noticed.
Another time I met a guy who had been hit by a car a bunch of days earlier, and upon checking over his bike, was riding with a front hub with a bent axle, super hard to turn it. He was oblivious to this and noticed it was hard to get going but once going thought it "was fine"
so yes, first hand knowledge is useful
-second thought. Years back some friends did a hotel trip and for various reasons they booked every
night (week long trip ish) but then bad weather either put them off schedule or they had to hump their keesters to keep on schedule, I don't recall, it was many years ago. All I recall is initially saying that it didn't seem to me to be a good idea to do that, but they were nervous about not getting a place and wanted the reassurance of it all before.
IMO not the way to do a trip and could easily work against you if you have this type of personality bicycle traveling.