You are absolutely correct that usually, the simplest way is also the best.
When you have a tonal goal and can achieve that with bass, amp and your fingers, that is good.
If you plug a few pedals in between, those pedals you consider essential,that is good, too.
If your tonal goals require multiple pedals, that is good, as well.
If you use 5 pedals, one of which is old and beaten and the switch is a bit wonky, while you could use one pedal to reach the same goal - well then the path with the one pedal might be better.
It's all a matter of what one is trying to achieve.
I've seen a band once that had two guitarists. One was playing a strat into a tube head. His pedalboard held a boost, a wah and a tuner.
The other guy played a PRS custom into what looked like the loot of the biggest boutique pedal shop heist in recent history. He had more than a dozen pedals active at times.
The strat did sound like a rock guitar is intended to sound while the PRS did not have much of a guitar sound left. (Meanwhile the bassist played straight into the amp)
This would show that at least in this instance, less is more.
Then OTOH I've seen bands with huge pedalboards where the players were able to harness that power to blow your socks off. In these instances more was more.