Windows 2000/95 Palm Vx compatibility

We are getting ready to upgrade our 95 clients to Windows 2000 clients and have a concern with our high level Executives compatibility between their office pc, laptop, and palm pilot. They use offline folders (.ost) with Outlook 98 (soon to be Outlook 2000) and then in turn synchronize that with their Palm Vxs. Concern being laptop running Outlook 98, PC running Outlook 2000, and then interaction with Palm. Any words of wisdom on issues encountered? Multiple platforms of laptops also, Sony, Toshiba, Micron, Dell, NCS, NES, etc…