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i'd say canon 50d and some good glass (16-35mm L, 24-70mm L). i'd shy away from the 500d if i were you because it doesn't have a wheel on the back that controls the aperture. you would have to press the av button then rotate the dial you normally rotate to change the shutter speed. it can be a tricky process for someone with two good arms.
i noticed a big difference between digic 2 and digic 3 (canon 20d to 40d), but not as great of a difference between digic 3 and digic 4 (canon 40d to canon 5d mkii).
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