Thanks for the good link boomertech!
I spent a long time getting my recorded guitar tone right, and it paid off in live settings. The most important part for me was stacking pedals correctly so that the tone I needed came through. For example, the OCD had to be hit directly with the guitar or it didn't quite make the sound I wanted. Anything before it was true bypassed to ensure that this happened. The same held true for other pedals going into the pre amp of a tube combo. The pedals I had in the Fx loop were also carefully selected so the tone wasn't degraded, or true bypassed if I really wanted the effect.
When I switched to bass, I found I was able to be less picky, as the changes from *most* buffers didn't cause unwanted changes. In fact some buffers (Moog LPF) for example were completely welcome when they were avoided on guitar. All this said, it comes down to what pleases my ear, and tone is a huge part of what I enjoy.
Further to all of this, what I have learned is that you can have a 25 pedal long system, play though it and make sound. If you spend time understanding how the pedals react to each other, you find combinations that make YOU come through. It's not magic, but it sure is nice to connect to and feel what you are putting into the sound, rather than have a pedal sterilize that out of it - even in a 2 pedal chain. BTW - the YOU part is the magic.
As long as you are getting what you want at the speakers, bypass method doesn't matter. True bypass is one way to help to get there, but not "the" solution. Good buffers should not take away, but should help when something else is taking away.