If what you are saying the Verizon CS reps are saying then yeah they are BSing you. Outlook does not sync via the internet unless they are talking about having an Exchange server to do push email (which I'm pretty sure that isn't what you are talking about). WIFI is free to use on the phone providing there is a wireless access point where you are at, you don't need a data plan for this. You only need a data plan if you want to have access to the internet where ever you go (providing you still have cell phone service) without having to worry about being able to find a wireless hotspot.

So, your roomate is correct and you do not need a data plan to sync with outlook on your home PC (whether it is via wifi, bluetooth, or USB).

edit: g@d d@mn I must type slow because someone beat me to it again.....