I finally pulled the trigger and ordered a Blackberry and mobile data service today. I really wanted to go through Amazon.com because I could have gotten the Blackberry for $100 cheaper but I couldn't get it to work with a data plan, only voice plans on Amazon.com. I ended up paying $100 for it plus a $35 activation fee. I will pay $29.99/month for an unlimited data plan. The sales guy assured me there would be no problem connecting to my Apple computer through the BlueTooth connection.
If this works I'll drop my Cable for $60/month and this thing will pay for itself in 4 months. I only had to sign up for a 1 year contract. In the remaining 8 months I'll save $240 total and have the benefit of being connected to the internet no matter where I am. I can't count the number of times I've been looking for a store or restaurant and would have liked to have google with me in the car.
If it turns out to be total crap or too slow I have 20 days to return for a full refund by state law.