This is an interesting post by rockyour guitar on reddit:
+ True bypass is better than buffered bypass.
Not true. I discovered this when I built my new pedal board. I made sure all the pedals were true bypass. I had over 15 pedals on the board, and it presented a problem. When I plugged my guitar directly into the amp, it sounded great. But when I compared that to running guitar > pedalboard > amp, I noticed a massive change in tone. Firstly, the volume dropped by about 10%. Secondly, I lost most of the upper range tones in the eq (ie. the sparkle) disappeared, leaving my tone very 'muddy' sounding. To solve this, I placed a buffered pedal at the start (TU3 Tuner) and the end (DE7 delay) of my pedal board and wham! my tone was back.
I heard this problem best described by John Mayer..
"Think of your guitar cable as a hose, and your guitar only pushes a certain amount of water pressure out of it. After a certain length, you’re going to need some more pressure to squeeze the water out. True-bypass takes the “in” and “out” cables of a pedal and connects them as if they were one long hose. After a certain length, you’ll get some pretty hefty tone loss. I learned this when I unplugged my guitar from my pedal switcher and went straight into the amp. Guitar pedals without the TB serve as a buffer for the signal, and naturally keep that water flow going. Yes, sometimes the trade-off can be harsh; some pedals, while buffering your signal, can also adversely color it, even when in bypass mode. That’s a good time to think TB. True bypass is a concept that only really took off as a selling point over the last 5 years or so. It won’t kill you to have it, but it certainly isn’t the only reason to get a pedal over another one without it."