When I got my Verizon Blackberry 8330 back in October, I first tried to use the free Pocketmac software from RIM to accomplish syncing it with my MacBook Pro. That worked a couple of times then blew up, taking my calendar and address book with it. (Luckily, I had backups.) Shortly thereafter, I bought The Missing Sync for Blackberry from Mark/Space and it's worked OK for the most part.
Yesterday I tried to sync and there apparently was a corrupted record in iCal and on the Blackberry, which kept causing the process to hang. Eventually, I downloaded the Blackberry Desktop Manager software for Windows on my Dell PC at work and used it to clear out the calendar on the Blackberry. (The Missing Sync cannot do this, which is a PITA.) I also made the mistake of clearing my work calendar which syncs to Entourage, which wiped out my work calendar. After an OH SHIT moment, I was able to restore my calendar entries by going through my Entourage folders and reaccepting meeting invites and manually readding some events. Not ideal but I'd been lax in backing up my Entourage identity, something I subsequently fixed.
Anyway, last night I went to Mark/Space's website and noticed that they had a free upgrade from v1 to v2 for folks who bought TMS between 11/1/08 and 2/9/09 available. I installed it this morning and was able to sync pretty smoothly. One nice feature that v2 added was syncronization via Bluetooth. Previously, it was USB-only.
What I'd really like to see would be for Apple to add Blackberry support directly to iSync, which is part of OS X and which some apps, including TMS, rely upon. I was able to use iSync to maintain the contacts on my Motorola RAZR V3m and it worked pretty well.
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