If you already have a wired connection, and it does what you want, and you can understand that, then once a WiFi connection is made the apps will work the same. Don't worry about how it does it.

As for syncing there are at least 3 different programs that will do what you want with the Pre, and wondering how it is going to do it over the WiFi is unimportant. Check out the various Palm Pre forums to get an idea of what is in use.

To find out if you have WiFi is important, but you didn't tell us what sort of computer you have. Is it a desktop or a laptop? If it is a recent laptop it is more than likely to have WiFi.

If all you are using Outlook for is the calendar, then you might consider switching over to the FREE Google Calendar, which allows you to access your calendar (and you can have multiple calendars) from any computer on the Internet. Plus, the Palm Pre already gives immediate access to multiple Google Calendars now. All the update and syncing is done automatically.