Can mail be exported from Apple's email on OSX to a Windows XP box running Microsoft Outlook?

Macboy - From apple mail you can export .mbox files, which I believe can be imported by outlook. You might want to run a test first - sometimes getting the inclusion of subfolders under your inbox can be tricky.

Actually, you don't need to export mbox files from Mail.app--that's the native file format for it. Just navigate to ~/Library/Mail/Mailboxes. Just copy them over. I'd be surprised if Outlook couldn't swallow them.

the subfolders will at least get squashed into the main inbox, as mbox files don't support subfolders (or folders, for that matter. It's just mail messages concatted, with "From" lines used as separators (not the from headers but real from lines)).

Outlook isn't swallowing... Other ideas?

I think the Apple Mail mailbox files are sort of confusing. I had similar problems, and finally realized that those Apple Mail mailbox files are packages, which contain lots of metadata in addition to the mbox. If you open the package, I think you can drag out the mbox and import it normally into mail applications that support that format.

I haven't tried this, but — does Outlook import Eudora files, like Outlook Express? If so, get http://www.eudora.com/ (or an http://wso.williams.edu/~eudora/kens/eudora.html), import the .mbox files into Eudora, go into Outlook and import the Eudora files. The second link above also has more information on converting to/from various formats via Eudora. Good luck.