I'd be very dubious about buying a second hand lens, given the price of that new ~£1400 you'd expect that it's been looked after but im not sure if i'd take the chance, for similar money you can get the 70-300 4-5.6 IS USM granted a stop slower, but you get IS and it will be new.
What you looking to shoot? sports, wildelife, motorsport or as a longer lens for portrait work?
The 580 lets you command other canon flashes, so if you're going to buy more canon flashes this would be the place to start, most people buy a brand flash or one that does TTL for on camera work and then cheaper ones to use with radio triggers, meaning that the extra you paid for the commander functions is pointless.
The 580 will also have a high guide number (it's brighter) than the 430, but the other features a canon user will have to tell you

Stink's probably your best bet as I think he's got both

Re the primes, it's defiantly worth having 1 or 2 as you don't have to worry about distortion; you know they are rock solid and they are so quick