have you seen my FAQ's?
BlackBerry Connect - BlackBerryFAQ
One issue that does re-occur and is a complete PITA is that when the device os gets upgraded you might need an updated version of the BB connect sw for it to work. As certain device manufaturers (e.g. SonyEricsson) provide the users with 'upgrade software' as standard (similar to windows updates) then it's possible for end-users to easily break a working solution.
To my mind connect is fine for single/couple of users but try deploying 50 devices and you'll just have headaches...
bb