A more automated solution might be to do it via Google Calendar. This is what I did for my Blackberry, Thunderbird and Rainlendar. I never actually use gmail or google calendar except as a sever for syncing my laptop and blackberry. Instead of trying to sync them with each other I sync each one with Google calendar.
This article talks about syncing Outlook with Google Calendar Sync outlook/google cal
- Warning: I don't use Outlook. This is just the first solution I found by Googling. There may well be other/better ways to do it.
The registered version of Rainlendar can also sync with Google Calendar so you can then use Rainy to update Google Cal and that will then sync with your Outlook automatically.
That just leaves your Blackberry. You could just continue to sync it by connecting to your desktop/Outlook but a better (mobile) way would be to use Google Sync
. That will allow you to add events on your BB while you are out and about and sync to Gcal. the new event will then automatically appear in Rainy and Outlook when they next sync.
Note: I also synced my Thunderbird address book with gmail using Google Sync. It sends both Cal and Contacts to my BB (two way sync) so i never need to connect my BB to my comp except to transfer media.
Check out Kigoo
which appears to sync both outlook cal and contacts. Might be a better solution than the one above. Warning: again I just found that as the first google search option. There may be many other/better ones out there.