Best you can do is try to estimate how much you use the 3G.
If you're almost always using the iPad near WiFi, then you may not need the unlimited internet and be able to save some by buying the lower capped tier later on.
Also, if you don't think you'd ever use more than 2GB of 3G, then there's not point in rushing since the $29.99 plan is just becoming a 2GB cap plan as I understand it.
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