I am planning on going with the 430 first, personally. It will be a smaller investment that will still allow me to learn how the speedlights work with my camera while providing a lot more potential than the built in flash.
If I start doing a lot of portraits, I can get a 580 also, and it can serve as a wireless master and the 430 I already own can now act as an off camera flash slave.
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Canon EOS (500D) T1i, PowerShot D10
EF 50mm f/1.8 II, EF 75-300mm f/4-5.6 III, EF 24-105mm f/4 L, Tamron 90mm f/2.8 Macro
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