I'm sure you will get more advice from mac users on this article. But you seem to be well on your way, its a great balanced real world review piece.
Since you ponied up for Microsoft Office I would not waste a lot of time with Appleworks. AW is almost "legacy" software for the Mac now, and has recently been superceeded by Pages. Considering what you have to get familiar with, Word and Excel on the Mac are very good, some think even better than their native counterparts. I would just dig in with them and save the effort for other Mac-centricities.
Internet Explorer on the Mac is now abandonware, and if you need some of its functionality with specific sites often Firefox will do it for you. Having it on the machine will not hurt (unlike in its native enviroment) but maybe some of the time saved on AW can be invested in Safari which is a very good browser. You might grow to like its simplicity. Once Tiger is shipped and RSS comes to Safari you might be able to ditch Firefox. In any case, maintaining duplicate bookmarks in both is not hard. Just leave IE if you can...its slow compared to FF and Safari.
You will find Vitual PC to be virtually unusable if you go with its stock XP install. (at least I have.) Molasses slow. And with the security center turned on, every time you launch VPC it goes and checks and downloads updates (SP2) automatically, basically making it unusable in the process. You really have to set aside some time to do updates when you don't expect to get work done on VPC.
Win2k is the choice here, it's very usable. Dig out an old install CD and fire it up.
Finally, you can use the system while updates are being installed, and very often there is no reboot. No need to switch to the windows laptop.
Enjoy the best of all worlds.