With the exception of using different stands, I use the hardware to mount the softbox and 580ex for a portable kit of mine, and they work well.
But some food for thought.
Buying a 580ex is about $380. An Alien Bee 800 is more powerful, and about $100 cheaper. All the accessories are made to work together, so you won't need to hodgepodge anything together.
I built a portable kit based on 4 580ex strobes, 2 med softboxes, 2 umbrellas, speed rings, custom made snoots and grids, barn doors, etc, and spent far more than a similar setup with WL800ws monolights. But it all fits in a medium sized tripod bag! I paid for portability, and compromised a bit on ease of use to do that. So I would heistate to add anymore speed lights to your setup, and go wtih something like the Alien Bees, WL, or similar.
With that said, you already have a 508, access to a second one, and a 430. You can easily make a nice little portable portrait setup with that. Depending on the variety of work you want to do, either umbrellas or softboxes will work. I would take the time to read up on the differences in the light quality between an umbrella and a softbox, and see which you like best. They are both pleasing, just different. You as the artist get to make that decision. There is some good info here; http://ksp.webphotoschool.com/index.html
. I think PhotoFlex has some comparisons on their website as well.
As mentioned by CanonCam, use one light off camera and play with it. Soften it with diffusion, move it closer, further, create shadow patterns by putting a plant in front of it between the subject, use a cardboard tube to act as a snoot for 40's hollywood glamour images, etc. You will learn so much more by doing that than starting with a whole bunch of equipment.
Here are a couple one light images. Very easy to do, quick to setup, and they turn out pretty reasonable results.
One strobe with a grid.
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One strobe with a softbox and close to the subject.
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One strobe with a softbox fairly close and feathered.
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You really don't need a lot of lighting equipment to get decent results. Take one strobe and play with softlight, hard light, feathered lighting, diffused, snoots, etc. Once you get bored with that, add another light and try mixing the lighting types such as hard and diffused, snoots and grids, etc. Also add in contrast ratios between the two lights. You'll get some very creative and excellent images by doing this, much more so than by starting with the standard softbox, fill, and hair light. Once you work up to three lights, you'll automatically know how to setup the traditional portraiture ligthing just by looking at a well lit portrait IMO.
Just a another way to approach learning lighting, which also happens to work very well if your lighting budget is tight.
