Question everything and do your own thing.You guys never question those rules of thumb when you've only got a couple things in the chain tho? I basically just crank the knobs on my delay pedal all the way (I play a lot of ambient guitar, so sue me) putting the compressor after it is creating this awesome effect where it masks the decay a bit and makes it feel like an infinite repeat that gets autocleared when you play your next phrase. But there's some other obvious "cons" to it.
Maybe you guys have long enough chains that you never dink around enough with stuff like this to have input beyond the rule of thumb?
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This is my current setup I've been using lately. I haven't quite decided if I like the Dark Side before the boogie pre-amp or in the effects loop so I end up swapping it around here and there. I will also swap the volume pedal over to my midi controller as a expression pedal for certain stuff.
I think in the older dark side it has an insert jack so you could put the delay part into the loop and keep the fuzz up front.
I would just decrease the volume of the looper. Adding more volume to an already muddy sound will just make it more muddy.