Well. I have a Boss RC20XL, an Akai Headrush, a T.C. Electronics DittoX2, and the pride & joy, a Pigtronix Infinity. I found the Boss to be frustrating in that it only sounded good to me when you processed the guitar signal first and then went into the microphone input. This is do-able, and a lot of people have done cool things with it - I assume you've seen the contest entrants and winners from the Boss contests? They're all over YouTube, and I actually can get some ideas about things to try.
The Akai was an early stab at an ultra-simple, on/off/overdub thing - it doesn't store any loops, and the maximum time is (I think) 26 seconds. It sounds quite good, but it is really just a looo-ong delay pedal. The Boss will save 9 loops, but that basic architecture came out before computers went blooeey! I think the newest Boss's have some sort of connectivity - offloading and reloading loops, if you want to save stuff up. But for me, the fact that I had to run some preamp stages before it, which then added to the classic Boss chilly tone. There's nowhere you can PUT a gate in there. I'm keeping mine around because I AM going mad scientist loopy, it might come in handy.
Before I got the Pigtronix, I looked really, really hard at the Digitech models (I like Digitech) and the Boomerang, which was surely the prevailing choice among people playing live, unless they were full-on mad scientists and went in for one of the $800 Oberheim rack units. The Boomerang is huge, and has some funny shortages in storage and such. And the Digitechs are a lot like the Boss - they're still piling more features onto the same basic architecture they've had for years.
What really sold me on the Pigtronix was
A) the advertising claim that it sounded GOOD, meaning you can go straight into it without a preamp boost adding noise. When you add even a little hum RIGHT AT THE BEGINNING it just multiplies, and multiplies. And:
B) I wrote Pigtronix a fairly stubhead-y e-mail explaining that I also played steel guitar, I don't have time or space to go crawling around on the floor to dick with some damn thing that has footswitches AND fingerswitches. And it's beneath my dignity. I think it's really weird in this day and age that guitarists still have to crawl before they can rock... So Dave Koltai, the owner of Pigtronix called me up and offered to build a custom footswitch so I could keep the Infinity right by me. (This is the way to a consumers heart - act like you GIVE A FOCK). And it works like a Howling Mother and sound great. And, it's got some heavy-duty computer innards inside, they keep updating it for different effects. I mean, you can configure it to have a pitch-shifting function, I think it's up and down two octaves - with any of the half-steps in between. Which I don't need, but that's the fun, you can set it to what you want. Electro Harmonix & Boss both make a whoopie out of the half speed function - record a bass line at double speed, then drop it to half speed an octave down. (?) I have two quite good pitchshifters hooked up, the Boss VF-1 & Digitech RP250, which makes more sense to me.
And then in order to get truly quadraphonic, I'm running a T.C Electronic Ditto X2 in parallel. I can loop either looper's loops through the other guy, using the mixer, but that gets noisy and prone to the really evil electronic feedback easily, so I haven't been fooling with that much. The Ditto is a much simple unit ( you don't to read the manual and spend days figuring it out like the Piggy), but - it also sounds real good. The Boss & Digitech units at this point are sort of... old-fashioned. I have a feeling that Boss & Digitech MUST be working on their next ones. It's like amp modeling or... cluster bombs for that matter - the lead in who has the best shifts from company to company and they all steal relentlessly. Right now Pigtronix & the Boomerang have the lead, T.C. makes the high-functioning bonehead stomper, Electro Harmonix has sort of a mixer-based one out now, the 45000. I can't remember why I didn't want to get one, there's something it does or doesn't do. Maybe it was that it just doesn't WORK without buying the footswitch for another $100 or so.