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I use OS10.2.2 with VPC5.0.4 running 98SE to ActiveSync and Outlook contacts sync with my iPaq 3955 (3835 previously) daily via USB without a single problem. The 3955 is brand new and I installed over 19 applications in less than an hour and half to it from .exe and .cab files downloaded from Mac Internet Explorer and accessed through "shared folders" within VPC. I drag and drop files to my FAT formatted PCMCIA hard drive and SD cards on the Mac desktop. It works so well, I see no need for PocketMac (although I appreciate their efforts to expose Mac users to the joys of PPC).
One thing to keep in mind about VPC is that XP with VPC has major problems consistently recognizing USB connections (not good for frequent syncing), often finding the USB driver missing after a restart or from a "saved state." Not sure about 2000 and USB, but I can highly recommend 98SE for PPC connections with your Mac.
Agree about RAM - get the maximum your iBook accepts - OSX loves RAM and nearly all complaints about speed are resolved having RAM available to eliminate page-ins and page-outs (UNIX for virtual memory writes to disk). Several superior Mac User websites:
xlr8yourmac.com
macosxhints.com
macfixit.com
macintouch.com
Much to learn and outstanding help from users, some experts; the best in the field. A visit to these sites display the community and sharing Mac users enjoy, very much like this site!
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