I have had 2 580EX IIs used mostly off camera with PW Plus IIs for triggers. They have also been used on camera for events. I have recently added 2 more LumoPro LP160 manual flashes. Two more 580EX IIs are suppose to arrive tomorrow.
The advantages of the 580EX II vs the 430EX II are:
1) Higher power, about 0.5 f/stops.
2) Build in pc-sync connector
3) Can be a master or slave in Canon wireless system
4) Head rotates 180 deg in both directions.
5) Can use external batter pack (faster recycle times, 3x more flashes before batteries die).
How important these advantages are depends on how you use flash. If you shoot wedding receptions, the battery pack will come in very useful. You can use the battery pack on light stands to speed up your recycle time, although this probably only makes a difference near maximum power.
By the way, the built in pc-sync connector on a 580EX II is a screw type. You can use the default cable that comes with the PW plus II, but it does not make a reliable connection. I had to tape them in to get reliable connections until I bought pc-screw PW cables from FlashZeba. You can use one PW plus II to fire two 580EX II in an Apollo Orb for example, using a splitter. You have to be very careful with splitters though. Don't ever connect them to two different kinds of flashes. The flash generates the sync pulse. All the pocket wizard does is close the circuit. Not all flashes have the same sync voltage. A flash with a high voltage sync could damage a lower voltage sync flash. The LP160s would not work at all when connected to a splitter, but they have an optical slave, so it really isn't needed.
With a 580EX II, you can run a E-TTL cable into a 580EX II in the Orb, then use that to control any other flash inside the Orb. This should allow you to control your flashes in the Orb from the menus on your camera. I'm not sure how you trigger other flashes outside the Apollo in this kind of set up. I could trigger the LP160s as optical slaves, but none of the Cannon flashes have that option built in, although it is possible to get optical triggers fairly inexpensively, you just need the ones that can ignore Cannon wireless pulses.
I would recommend getting at least one 580EX II. I think the older 580EX I lacks the pc-sync port and has a plastic foot instead of metal. The 580EX I also is suppose to recycle a little slower.
What you get all depends on what you want to do. If you want to fight with bright sunlight outdoors, even the more powerful 580EX II is marginal. Two 580EX IIs in a soft light modifier, like a softbox or shoot thru umbrella, have to be kept close to the subject to fight bright sunlight. Of course if you use flashes bare for hard light or if you position your subject in the shade with a shaded background, then it is not a problem. If you want to fight bright sunlight, you should think about buying some kind of battery powered studio strobe. Something in the 400w/s or 600w/s will be a big improvement (A 580EX II is probably about 60w/s equivalent).