I think it also may depend on how you would like to run windtab - the higher rate plans do give a larger front-end discount than the lower rates (not sure of the exact numbers).
I also wanted to check in and say that (so far) the $5 preferred roaming to the US (10 cents per minute) seems to be working flawlessly (will find out for sure when I get the bill). It auto connects to T-Mobile and have had good service with really no hassles. I am using it as a phone (no data) and like the convenience so far.
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