Watch this scene from Harry Potter and Sorcerer’s Stone:
I recently re-watched this wonderful movie, and when I heard the line: “The wand chooses the wizard, Mr. Potter,” it struck me that it seemed as if the drive pedals I purchased sort of “chose me.” Like Harry Potter trying out magic wands, there were some that I tried (and bought) that were so harsh they seemed to throw things around the room. Some were so funky-sounding, that they’d break things. But then there were four that spoke to some inner part of my being that seemed to fill me with creative power. Those were my Timmy, Tone Freak Effects Abunai 2, and my EWS Little Brute Drive, and Creation Audio Labs mk.4.23 boost. I may get other drive pedals in the future, but those will always stay on my board. They’ve become an integral part of my tone.
I suppose that this goes for any gear that I have, but my search for the right drive pedals was long and expensive; not necessarily in terms of money, but most especially in terms of time. I tried out hundreds over the years, but none have moved me as much as these four. And frankly, that “moved” feeling is the main criteria for me purchasing drive pedals.
Of course, I can’t play everything, but I do a lot of research before I buy. To me, a drive pedal is an incredibly personal piece of gear. I can’t just play any drive pedal. Some folks might be able to do that and sound good, but my ears are particularly sensitive to drive sounds. If something is off, just by a bit, then it bugs me to no end. Can’t necessarily describe the exact sounds I’m looking for in a drive pedal, or what might turn me off, but I do know when I hear something that I just have to have. Then I’ll buy it.
Guitar Gear 
I’m with you on this one, Some pedals like the Timmy work great on many amps and some only work good on one or two types of amps. My go to pedal is the Lovepedal Eternity Burst when I’m playing a mesa or fender type amp. And also my Fargen Menatone VOS which is a great pedal and one of my favortes is a little more “picky” on who it chooses to play with.. THat being said you can’t beat a modified 808 clone like the Bodenhamer Bloody Murder which is no longer in production. .
I still have my 808. Never play it, but I’ll probably never get rid of it as it has some sentimental value – it was my first drive pedal. I might just put it back on my board as I’m now playing different amps than when I first got it. Maybe it’ll speak to me again. 🙂