I'm not sure about the varients of Outlook and how they operate. For basic outlook express that we have on our network with win2kpro, it's that simple.
RealNames: as wyvern said above you burn them to CD, or network the 2 PCs, or use a zip disk/stick or something to get the files across.
I've done the process many times and it's usually as simple as exporting them, and then importaning them and everything usually keeps its same structure.
I am not a Windows user, but I admin a Windows network and know how great their "wizards" can be.
I know it's off topic, but I really do suggest you take time to learn more about Unix-based computing. You will never want to use Windows again! (ok maybe for Photoshop, but that's about it!)