The only challenge? Getting my calendar and contacts onto my iPod. So far I've found a couple of options.
The first is from AppleScripter Paul Berkowitz. Paul has created two scripts for this purpose: the aptly named "Sync Entourage - Address Book" and "Sync Entourage - iCal". Both are shareware and each cost $19 which includes lifetime updates and bug fixes.
The second is iPod It from ZappTek which costs $14.95. I'm unsure if that includes updates.
Right now I'm trying out Paul's scripts. The iCal script worked perfectly and I'm in the middle of an Address Book sync. My guess is that it will work fine, too.
Update: It also worked perfectly.
That said, iPod It may be the winner, even though I haven't tried it yet.
Here's my thinking:
Paul's scripts require three steps: 1) Sync Entourage with iCal; 2) Sync Entourage with Address Book; 3) Sync iCal and Address Book with the iPod.
iPod It performs a sync in one action AND it will also transfer Tasks, Notes and Email. Plus, it's GUI is a lot friendlier than Paul's AppleScript installer. Finally, it's less expensive ($14.95 vs. $38).
ZappTek also makes iPod Launcher - automated iPod detection software which integrates completely with iPod It. So, you never have to remember to sync your data again: each time you plug in your iPod, it automatically syncs with Entourage. Very cool.
So, providing I'm happy with the results, a purchase of iPod It and iPod Launcher will likely be in my future.
Update: Or not. I found some inconsistencies with the calendar sync.
For instance, it has today's 10 AM appointment listed three times in my schedule. I think it has to do with the classification of the event.
iPod It imports calendars based on their category. For reasons yet unknown, it has my 10 AM appointment listed once in each of my "Work," "Other" and "Weather" calendars. (I chose to sync weather reports, too.) So, when I view "All" calendars in a single instance, the calendar event shows up three times.
I'll have to see if I can make some adjustments to get it functioning properly