I have a Carl Martin Compressor first in line in my pedalboard, followed by three true bypass pedals. Last in line is a Boss DD-5. When I replace the DD-5, should I go for a delay with True Bypass, or is a buffered pedal suggested as my last pedal in the chain. I do leave the pedal on 80% of the time, so maybe this won't be an issue, but I thought I would check with those who know more than me.

well, just try this. unplug your delay and go from the last pedal before the delay into the amp. if you notice any signal loss or change in the pedal tones, then you need a buffer at the end. if not, then your free to do whatever.