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I'm about to purchase my first flash and I'm thinking about getting the 430 EX II, but I'm worried that I might end up regretting not buying it's bigger brother. Should I just spend the extra $20 and get the 580 EX II?

First off, the difference in price is $165 USD on B&H, not $20 (I think you meant to say $200).

Look at the differences. The 580ex II...
...is heavier
...is larger
...is more powerful - I have read that its 85% more powerful
...is weather sealed
...can turn 180degrees both left and right (430 is 180 to the left, 90 to the right)
...tilts -7 deg. to 90 deg. vertically (430 does not go -7)
...has a built-in catchlight card
...can be a wireless transmitter and a master controller
...has a wheel on the back instead of buttons
...has a socket for an external battery pack
...has an external metering sensor
...has a pc terminal

It costs more, but you get what you pay for. If I were you, I would definately get the 580ex II. Later on, you could always buy a 430ex II to use in addition or as a backup.

EDIT: I forgot to mention...the 580ex II has finer control. It can go from 1/1 power down to 1/128 in 1/3 increments. I believe that the 430 can only go to 1/64 power in 1 stop increments.

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I had the same dilemma a few months back but decided to go safe and went for the 580EX II. In the end I didn't want to be "thinking what if I'd bought the 580Ex instead..."

Trust me you won't regret it.

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Canon EOS 5D MK2, EF-24-105mm F/4L, EF-50mm F/1.2L, Speedlite 580EX II
http://www.flickr.com/photos/2ndtake/

Had the same problem but I ended up getting the 430EX II. I say both flashguns are very good. It was kinda tight for me financially so I took the 430EX II but no regrets. Its a very good flashgun & I think practically I don't need the features of the 580EX II (at the moment anyway...for my needs) and can always upgrade in the future...but that's me. Enjoy whichever you choose...you'll have fun using it.

I went with the 580ex II for 3 reasons...

1) more powerful so better for outdoor wildlife shots requiring fill lighting.

2) has the capability of being a wireless transmitter for slave flashes.

3) weather sealing.

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Canon 7D + 50D + EF 100-400mm f/4.5-5.6L IS USM + EF 24-105mm f/4L IS USM + EF 100mm f/2.8L Macro IS USM
Pelican // Black Rapid // Think Tank // Manfrotto // Garmin

Reflections On Canadian Wildlife
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I went with the 430 myself-

My camera isn't weather sealed, power is adequate for my purposes at this time, wireless master is no use if I don't have a slave and if I get a 580 in the future I can still use my 430 as a fully ETTL slave.

I'd love to have the 580, but I would have been looking at another $200. I'm going to spend that extra $200 on some cheap RF flash triggers and a couple old manual flashes.

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Canon 1000D, EF-S 17-85, EF-S 60mm macro f/2.8, EF 50mm f/1.8, Tamron 70-300, 430EX II

I also went with the 430EX (non-II). I am very pleased with it and have had zero issues with it.

I bought it before the 7D even existed but am happy I saved the $200 since the 7D has built in remote flash triggering. I could probably use the extra reach of the 580EX at times but that hasn't stopped me from getting good shots with my 430.

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Canon 7D, Canon EF 24-105mm f/4L IS USM, Canon EF 70-200mm f/2.8L USM, Canon EF-S 10-22mm f/3.5-4.5 USM, Canon EF 50mm f/1.8 II, Canon Speedlite 430EX, Canon 7D Battery Grip, Canon 12mm Extension Tube.

PhotoBlog: http://www.ancker.net/photoblog/
Gallery: http://www.ancker.net/gallery/

430ex ii does this.

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Mark Osborne
My life through an iPhone

I know a pro who's won more prizes than I have taken pictures, and he uses the nikon equivalent of the 430 EX II...so I think you're fine with it. It should be powerful enough, unless you want to kill ambient in full sunlight

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I take pictures so quickly, my highschool was "Continuous High".

Read a little bit of "The Hot Shoe Diaries" (not porn) at books a million and after looking at some of the set-ups and results...well now I want both. . Why oh why couldn't I just have taken up rock collecting.

This is directly from Canon's site:
"The flash head can be moved up from 0 - 90° (5 settings), left from 0 - 180° (7 settings) and right from 0 - 90° (4 settings)"
Listed Here

Not that 7 degrees makes a big difference.

I'd also like to correct myself, the 430ex II does go from 1/1 to 1/64 in 1/3 stops, not 1 stop increments.

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My Site

Interesting after reading spawn's post. The 580 covers af points of 1, 3, 5, 7, 9, and 45. The 430s don't cover beyond 9 points. Also neither are matched for the new 7d's af points

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Canon 7D/350D, Σ17-50/2.8, 18-55IS, 24-105/4 IS, Σ30/1.4, 50/1.8, 55-250IS, 60/2.8, 70-200/4 IS, 85/1.8, 580ex II, 430EX II, 270EX II.

well my findings come direct from my flash, but canon has rehashed old settings by the looks of it

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Mark Osborne
My life through an iPhone

This is incorrect...the 430ex ii does not go to -7 degrees. That's a only 580ex feature.

I also own the flash.

Also direct from the-digital-picture.com

"While the Canon Speedlite 430EX Flash head moves up/down from 0 to 90°, left from 0 to 180°, and right from 0 to 90°, the 580EX II allows an additional -7° down and a full 0-180° rotation right. While both flashes feature a pull-out/flip down wide angle diffuser to cover lenses out to 14mm (FOVCF equivalent), the 580EX II includes a white plastic pull-out catchlight reflector panel in addition. The Canon Speedlite 430EX Flash features 6 custom flash function settings, the 580EX II features 14. Instead of a dial for adjusting settings, the 430EX utilizes rounded parenthesis-shaped buttons. I can understand making buttons safe from accidental changes, but these buttons are narrow and require an excessively deep press to make changes. The dial is much easier to use. "

430ex here also. At first it was the price deference is why I went that way. Then I find myself rarely using it but when needed, it works just fine.

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Canon 40D
Canon EF 24-70mm f/2.8L USM
Tamron AF 70-300 F/4-5.6
Canon Speedlite 430EX.