In my searching the past week I found many articles about how using VMWare and trying to synch a Blackberry using the Blackberry Desktop Manager failed. Many of these articles were 2006 and before – nothing more current. Well, I found the solution and present it here for others that are looking.
The best I can tell is that using any VMWare Workstation before version 6.5.x uses a very different method of attaching USB devices which is not direct. The Blackberry Desktop Manager uses a direct connection for security and other measures.
I use Windows XP SP2 to run VMWare Workstation and I am running Windows 2000 with SP4 to run the Blackberry Desktop Manager.
Have at it!