When do you decide to flip?

[Zeus]

If I'm not actively using it, or if I don't connect with it right away, it is gone. I don't really have any examples of successfully "growing into" something that didn't work for me right away, so my first gut instinct usually proves to be right.

Exactly this for me too. There's been a few occasions where I've hung onto things I haven't immediately connected with, trying them out in different ways, getting to know them better; in no circumstance has it ever been worthwhile, I've never had an 'aha!' moment weeks or months later.

I usually know within the first five minutes if I'm going to keep something or not. If it doesn't feel right then, it generally won't. Of course things will sound different with different guitars, different amps, etc. but I don't have any plans to change my guitars or amp, so...

I would go through way, way less stuff if I were able to try it out first but that's generally not an option. The buying/flipping process is just a way to see how things work in my set-up. Going into every purchase I'm aware that I might be moving it on.

[Iommic Pope]

I'd so buy a Space Echo/Jazz Chorus Roland green guitar.

Yes.
I was thinking the same thing it's a nice green.
Also good is RV3 metallic charcoal.
As is Ruby Sparkle Xtortion red.

[untilshewokeme]

I have flipped my entire (or almost entire) board 3.5 times in the past year or so. Many decisions have come into account whether the pedal was just to expensive and I couldn't justify it or I wasn't using all the features and wanted to try something else or just because I wasn't gelling with it.

I don't have the cash or space to have shelves of pedals not on my board so I see my board as something that is constantly evolving as I either try out different things or find harder to find stuff I have always wanted to try out. Each time I slowly narrow down and more and more pedals stay the same.

Since I am not in a band and just jamming either by myself or with friends, I don't have a specific sound I need to conform to (besides the handful of pedals I decided I'd never flip, using those as a backbone).