Using:
BlackBerry 8530 with v.5.0.0.654
BlackBerry Desktop Software v6.1.0.36
Microsoft Windows 7
Windows Live Mail

-- Okay, I understand RIM and Microsoft didn't get together to make synchronization easy, or even possible. Everything I have tried with the 8530 connected USB to my Lenovo Windows 7 laptop just doesn't work. I've turned wireless sync off. I've tried exporting a .csv file from Windows Live Mail. Name it, I've tried it. Including turning wireless sync on for syncing with my msn.com, live.com, and gmail.com email addresses.

Am I fighting a losing battle? I'd manually create a .csv file for all 88 of my Windows Live Mail Contacts, if that would work. Anyone else been through this? Should I give up? Keep trying? Purchase Outlook? And, thanks in advance.

Could you import your csv contact file into Gmail and then sync your gmail contacts down to your BB. This would eliminate having to use DM and could be done OTA.

Thanks jsconyers for the suggestion to .csv to gmail, then sync that to the BlackBerry. Experimenting with this, there truly seems to be NO standard from one email contact list to another. Imagine driving to a city where green traffic lights mean stop and every other block one must drive alternatively on the left side then the right side of the road. Well, in the case of address books and contacts lists, every vendor is on a system entirely their own. Coordination and cooperation are nonexistent. It is a mess, and I'm inclined to give up on having any two address books or contacts lists the same. Short of typing everything in manually for each device or email provider, I don't think there is really any so-called synchronizing of data. And I want someone to prove me wrong <grin>.