Ever since switching to the Verizon Blackberry Tour 9630 from the AT&T Blackberry Bold, I've been unable to sync contacts from my Mac. And yes, I am fully aware that Google Sync exists (thank you). I use it for calendar sync, but it isn't right for me for syncing contacts. Incidentally, the switch to Verizon from AT&T was the best move ever because my phone ACTUALLY WORKS now. I was just waiting for a Blackberry World Phone that didn't look like a brick. So far, my Verizon phone has worked everywhere except for one place: Ogasawara, Japan (Verizon has a deal with SoftBank and not DoCoMo).
In any case, I finally figured out what the problem was, and how to fix it.
The Blackberry Tour, running Blackberry OS v184.108.40.206, cannot sync contacts from Address Book that contain Custom Images taken with the iPhone or set using Address Book on Mac OS X (I'm on Mac OS X 10.6.1 Snow Leopard).
Contact images taken with the Blackberry sync back and forth just fine.
Because my contacts sync on MobileMe between my iPhone and Address Book, many of my contacts have Custom Images taken by iPhone or set from within Address Book. If I try to sync even a single contact that has an iPhone-snapped custom image, sync fails. In Blackberry Desktop Manager 1.0.1 (build 2), I get an error dialog that pops up saying that sync failed, and that I should "try again." The sync process stops at that point, and the log isn't useful because it only logs that last 200 lines or so. I can't find the error.
Missing Sync v2.0.3b5 also fails to sync these records to the Blackberry Tour. Its log is more useful, and actually lists the specific contacts that failed (although the error in the log is cryptic). Missing Sync continues after the error(s) and syncs all of the other records.
Note that I never had this problem when I had the Blackberry Bold, so something is different with the Tour, or perhaps the OS version it's running on.
It's funny -- when I first started having problems with sync, I remember wondering why it seemed to be failing most on records I used the most. My close friends' records were all causing problems! But the correlation was actually that I was more likely to set a Custom Image for a good friend than for someone I don't spend a lot of time with.
To find the problem, I did a manual binary search of my 1070 contacts, looking for patterns on the way. It took me 5-6 syncs to isolate a single contact that wouldn't sync.
For a successful sync of all my contacts, I had to remove all contact custom images in Address Book. It is a shame, because adding custom images is fun, and I like seeing the large photo appear on my iPhone when people call -- that is, when a call on AT&T actually comes through. Maybe it's not a big deal; I use my Blackberry most of the time these days, but mostly because it's on Verizon.
Jabba cake had to go!