Time to rock the boat i guess,
i have never had great joy pointing my parallels or fusion towards my bootcamp partition. It seems to give me rubbish and i end up redoing it anyways. If it works for u great, i always recommend to NOT do this.
O2m is great, but why not use thunderbird? its free, it converts ur mail, and mac mail can import directly form a thunderbird database file? With the $ rate, save what u can.
Again another difference of opinion, i prefer entourage, i find mac mail slow to read/download messages, it times out faster on slower connections, and it cant exchange. Entourage is also buggy, but i also like the fact it has DB files, easy to transfer/backup. I have also seen very corrupt mac mail situations, which is easier to fix on entourage.
But....instead of buying office, try using the new version of open office. its pretty good
I would format the drive hfs+, and use macdrive on windows if possible, when snow leopard is out, its easier to convert hfs+ to zfs.