I have what has been described as "the most extreme" calendar sync setup, and for good reason. Fortunately, my sync needs are not unique, though they are a bit ahead of the times. Eventually everyone will have some form of this sync logic in their workflow.
I have a BlackBerry Bold 9700 (recently replaced my Bold 9000), and I use Outlook 2007 in a virtual machine running on a Linux host. I have 6 separate calendars configured in Outlook, each in their own PST file. These cannot be merged, more on that in a moment. In brief, they are:
- Work Calendar
- Personal Calendar
- Cozi Calendar
- Holiday Calendar
- Archived Calendar
- Girlfriend's Calendar
In BlackBerry Desktop Manager, I configure these 6 calendars to sync to my BB, with the "Personal" calendar being the primary calendar source for any events added on the BlackBerry side.
I also configure 2 Work/Personal folders for each of the Contacts/Address, Tasks/ToDos, Notes/Memos items in BDM, again with "Personal" being the primary source for each of these.
When I sync, everything shows up on my BB, and remains separate on the desktop Outlook session, which is exactly what I need.
I do not want my Personal items showing up on my Work calendar, and getting pushed over to the work Exchange servers.
Likewise, I do not want my Cozi calendar items (which I sync to share with my ex-wife for my daughter's events) showing up on any of my Personal calendar items, or vice versa.
In Outlook, I have 4 profiles configured:
I log into my work VPN and launch my "Work" profile, which has all 6 calendar sources (all 6 .pst files) attached to it. I can "see" everything in one merged view in Outlook. Perfect. This is the profile I use when synchronizing to my BB.
When I want to sync items over to cozi.com, so my ex-wife can sync HER computer/iPhone to those events, I log out of Outlook (I use KnockOut to ensure it is fully closed), then I launch Outlook with my "Cozi" profile.
In the "Cozi" profile, I have the Cozi Outlook Add-in installed, and I have only one calendar source attached: Cozi.pst. I sync this profile to cozi.com's servers, then log out.
My girlfriend can add items to her calendar via Outlook in her own profile, or she can also log into cozi.com directly and add items there, which get sync'd to my local profile for her (which also has its own .pst file).
Literally NOTHING else I'm aware of, can do this without messing it up, duplicating events, causing mystery deletions, or adding items to sources that should not receive them.
Google Calendar is not an option, because synchronizing to Google Calendar will "merge" all of the items into one calendar source, and when I sync back to my BB, it will "flatten" them, causing me to lose any calendar source separation I have.
I've literally tried every commercial, free and combined solution out there to try to make this work in a platform-neutral, secure fashion that does not tie me to BlackBerry or to Outlook. There's nothing out there that does this.
However, the notion of "family" calendars, merged calendars and "group" calendars is very important, and becoming more important every day. If apps (like Google Calendar, Lotus Notes, Funambol, etc.) don't get with the program, they're going to rapidly fall far behind.
I'm not a fan of Windows, nor Outlook... but this works, and works flawlessly for me.
(p.s.: I know "sync" very well, because I'm the maintainer of the codebase that lets PalmOS devices sync on UNIX/Linux systems, which is also used by a lot of commercial companies on Mac and Windows under the hood as well).
I'd love to hear anyone else's stories, on how they've solved similar issues.