You will need to upgrade both the handhelds and the BES to 4.0. Upgrading the handheld can not be done over the air - you have to install the code on the PC and update the BB via Desktop Manager. Once that is done, assuming you are using Exchange as your infrastructure, everything is wireless - calendar, notes, tasks and contacts.
As far as VPNs go, there are several, including Raptor Mobile and Aventail. I personally like Aventail. All are hardware/software combinations.
The best reason for having a VPN is for providing network access remotely and securely (I am using Outlook via VPN to our office network); not only can I use Outlook, but I can sync my BB from home.
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