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Edward van Altena
Considering you're going to be going through the hassle of setting up softboxes on stands, I would strongly recommend that you should go with a studio flash setup instead of a hotshoe flash. You'll get a hell of a lot more bang for your buck.
Hotshoe flashes are great for what they're designed to do, which is to be something that you can mount on top of the camera. But you pay a premium for that type of miniaturization, in terms of both performance and price.
A Paul C. Buff Alien Bees B800 costs about as much as that 430 EX II, and it puts out so much more light that it's not even funny. The Buff Einstein flash, their flagship model, is cheaper than the 580 EX II and is ludicrously far superior in every way except that you can't stick it on top of your camera.
Don't fret too much if you're going to be shooting at locations without power. There are battery packs for most studio flashes. Buff sells the Vagabond which is good for hundreds, if not thousands, of pops with the type of setup you're describing on a single charge.
I'll also note that softboxes only work their magic when they're so close to the subject that you're having trouble figuring out how to shoot around them. It's a geometry thing...a 2' softbox is going to have to be no more than 2' away from the subject to be truly effective, preferably less, and it's not going to light up more than the person's face. a 2' softbox at the photographer's position of a 10' working distance isn't going to be significantly different from on-camera flash. A 5' softbox 5' away from the subject is going to be as effective as a 2' softbox 2' away, but it'll light up the whole person...and you can put that 5' softbox 3' away and get some amazing soft and even light wrapping all the way 'round your subject.
Buff sells parabolic reflectors...basically high-tech umbrellas. And they go from 4' across to over 7' across, and they make diffusers for them that make the light very similar to a softbox....
You might consider something with more get-up-and-go than a 430EX for what you're proposing. Punching a little 430 through a softbox or umbrella won't leave you with much useful output, especially outdoors. And your recycle times will be uncomfortably long. The 430 has an output of 30-40w/s, the 580 is around 60-65w/s.
For outdoor portraits in sunlight I often need to crank up my PCB Einsteins http://www.paulcbuff.com/e640.php up close to their maximum output of 640w/s. Einsteins are great but if you have severe budget restrictions, the PCB Alien Bees might be worth a look http://www.paulcbuff.com/alienbees.php. Skip straight past the lower powered models and go straight to the B1600. For working on location, PCB has extraordinary value battery packs http://www.paulcbuff.com/vagabond.php For umbrella/softbox check out the PLM's http://www.paulcbuff.com/plm.php.
The 430EX is a decent little flash but I think your expectations of what it is capable of are somewhat out of reality. If your are serious about the business you're starting up, do it properly and turn up to your shoots with equipment that will do the job. Even a 580EXII or 600 EX-RT will struggle in sunlight unless you are up very close to your subject...and that's without a modifier.
For portrait work it's important to get a flow going with your subject, and to have the capacity to shoot immediately without that mood-smashing wait while your flash recycles. Speedlight = slow.
You'll need a speedlight, and should have one...but be 100% aware of its limitations.
which brand of extension tubes did you use?