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When I feel like just getting rid of almost everything.
I don't really do too much in the way of flipping pedals, unless I need the money or space.
If I do buy a pedal, I'll tend to keep it unless it truly disappoints.
In all honesty I've managed to avoid too much disappointment by researching products prior to purchasing.
However I'll also keep pedals for a while even if I don't gel with it straight away, as my tastes have been known to change over time, and I often find pedals can work well in combination, so it's sometimes a case of finding the right combination.

When I feel like just getting rid of almost everything.
This is why most pedals have a bypass.Not even that. I just want to keep like, a distortion and tuner, if that.
i go through spells where i'm ready to sell off everything. i never used to sell anything, but over the past few years i've started to sell off stuff that wasn't getting used or didn't like anymore, and it's kind of freeing. i'll never get to jeff berlin level where i sell off everything but one bass, two combos and a chorus pedal, but i'm glad i sold off what i have. i don't really miss any of it. ok, occasionally i miss that 98 jazz bass i used to have, but it hasn't affected my playing any, and my shoulder sure feels better for switching to lighter basses.
Gear De-Acquisition Syndrome
Anyone else ever get those days, too?