I'd also double check the need for a Blackberry data plan. When my wife switched over to her BB Pearl, she had an unlimited data plan. Tried to get the BB to work with ANYTHING (email, web, etc...) no joy. Called Cingular and switched it over to a BB data plan. 5 minutes later, it was working as advertised.
Oh, and for 3rd Party internet/email programs good luck. My wife and I have been trying to get some of them to work with hers, and it's always a headache. Apparently there's some extra switch that must be flipped over at AT&T that we're missing. Either that, or the DNS information I was given doesn't work. Either way, I would hardly call it a painless install.