I've tried plenty of multi-effects and I've always prefered singles. Yeah, they're more expensive... but who cares? I'd rather get something I'm going to like instead of settling for something cheaper... they sound much more natural. Listening to digital overdrive / distortion tones makes me want to cry.
The only thing multi-effects are good for are home recording as far as I'm concerned... like a PODxt for example. Even then, I just bought a cheap mixer, plugged it into the PC, got an SM57 and mic'd the amp.
As for what pedals you'll need... it's up to the tone(s) you want. I use a MXR Wylde Overdrive to push the tubes, Boss CE-5 Chorus (soon to be replaced by a MXR Stereo Chorus) is always on to fatten up the tone, Dunlop Wylde Wah as a treble boost for some solos, MXR EVH Phase 90 for the occasional solo for a nice effect, Boss TU-2 for when I've tuning after putting new strings on and Boss GE-7 to shape my tone (soon to be gone, buying a KFK 10 band). Sometimes I'll turn a little reverb on the amp, the footswitch for the amp can turn it on and off so sometimes I use a bit on solos.