I think I will cut up my pst file a bit to reduce its size. Specifically split off a few contact lists that can easily be grouped together in a separate pst folder. As is my pst folder is about 4 gigs - Yikes.
I am still a bit unsure if this is going to be worth the $200 for the phone but I will have a month to play with it and see. If not then I just have a $35 restocking fee. $200 does not seem like a lot but it is the same as the HTC Evo with sprint - of course that requires the full data plan plus $10/mo for the 4G. And as I am dealing with a family plan everything gets multiplied.
As for the contract, I have been told that it is possible to use the winmo TP2 with just a messaging plan with sprint. This should be interesting... we shall see.