Does turning on something like a true bypass overdrive buffer your signal? Or is it still useful to have a buffer in a long chain? I'm curious if the signal degradation only happens when everything is turned off, assuming all of your pedals are true bypass.
No, degradation happens when there is anything between you and your amp. Look up some buffers on YouTube to hear the difference, it's pretty amazing.
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I would imagine that any pedal with a low output impedance would serve the function of a buffer for the signal path leaving that pedal. If that pedal is at the end of a huge pedal board, you might still need a buffer at the start of it to drive the signal from the pedal board input up to that point, since your signal is going through some amount of cable from your guitar into the board and through all the cables connecting your pedals before hitting the last pedal on your board. I think that's the idea behind having a buffer at the start and possibly end of your board.
I'm not super knowledgeable about impedance though so someone else might want to chime in and confirm this.