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the infamous -- chain my pedals query

I basically run my board in sections. For you, I would run it like this.

Bass
Booster
Fuzz
OD's
Analog delay
Digital delay
Reverb
Compressor
Looper

This way you send the boost to your whole dirt section for more/different gain, you've got your fuzz into your OD to get that fuzz into a cranked amp sound, you have your analog delay for warm organic sound that you can stack with your digital delay for crystal clear echoes of that warm echo sound, into your reverb, to a compressor to level out and tame those peaks and polish up the sound before it hits your amp or FOH.