I actually went the other way. I still have a few pedals around that i wasn't sure that i wanted to get rid of, but i don't find myself using them very much at all. I'll give you a run down of things i've owned..
Visual Sound
first off let me suggest that you look into Visual Sound's stuff. It's cheaper than most boutique pedals but they sound fantastic. if you haven't seen this, check out the pedal shoot out videos. you'll see a lot of the other things listed in here too.
http://www.youtube.com/visualsoundusa#g/u
Route 66 - this is a combination compressor and overdrive (based off of a Tube Screamer). First off, of the three things i've had compressor wise, this by far wins. The overdrive on top of it was amazing. If i were going to get just one pedal for playing through my amp when i wasn't using my LINE-6 stuff, this would be it.
Jekyll and Hyde - a dual distortion. you can use a crunchy distortion side, a tube screamer clone, or a combination of both. Super incredibly versitile and sounds great.
Visual Volume (i still have this, let me know if you're interested). I liked this volume pedal a lot because it has great flexibility (stereo, mono to stereo, tuner out) and the greateast feature are the colored LED's that allow you to see where you're rocking it. I tightened mine up a bit for more control, and I love it. I kept it for using on my acoustic or bass, but it turns out that i'm just not using it.
Liquid Chorus - Freaking amazing sounding. WOW. I had this the shortest time however, as it wasn't too long after this that i decided my board was too large and too complicated to use the way i wanted so i switched to digital.
1 Spot Power Supply - works great, but can't power all types of things. if it's all dc 9v stuff, this is the way to go.
Others
Keeley Compressor (4 knob version) - Sounded....fine. if you ask me, it was simply too expensive for what it is.
Boss CS-3 Compressor Sustainer (Still have this, let me know if you're interested) never actually used it, still have it. bought it in a package deal.
Pigtronix Ep-1 Envelope Phaser - This is one sweet pedal. It's large and AC unfortunately, but it's so customizable. you can do almost any kind of phaser with it (it can change waveform shapes), but it can also be used based on volume envelope. it's really cool. The model i had was modded to have some extra functionality, but the new versions include most of the mods. It's neat. necessary? naw. unless you're real experimental then go for a small stone phaser.
Rocktron Silver Dragon Tube Distortion. Another dual distortion. beastly sounding. one part is actual tube, one part solid state. you can use one by itself (not the other) or both. weirdly named knobs. I loved how this thing played through my tube amp.
Eventide Timefactor - freaking amazing piece of machinery. very expensive though. wow is it cool though. I'd highly recommend checking it out and playing through the presets, the all sound amazing. would i buy it again? not for that money. but if you're looking for some sick clean tones and/or play a lot of modern delay-y stuff, and money isn't an issue, i'd put it at the top of your list.
Danelectro corned beef reverb - pointless.
Boss Autowah - also pointless. this is one of the dumbest things i've seen. if you're interested in this kind of stuff check out that pigtronix pedal which can do this and more.
Let me know if you have any questions.
