Still having import problems.... Lost Cause???

After trying every possible solution (including upgrading 9.1 to 9.2 for Classic) that I can dream up or have read about, I am desperate for an answer. I have two potential Email programs that I could use in Tiger: "Mail" or "Entourage 2004". Either one suits me, but neither one will import my old email from Outlook no matter how I configure the import or where I put the actual "Messages" file. It's a huge file, at about 1000 MB. I've read that "Mail" won't import from Outlook at all, and I've read that Entourage should import this file.
What I get when I run the import function and click down to the Identities folder inside of the Microsoft User Data folder is grayed out files. It's not just the "Messages" file that's grayed out, it's actually all of them (Database; Signatures; Contacts etc.)
In fact, I just tried launching Outlook 5 in Classic to see if I could import there. Still no success, no matter which import format I select (as text or from application).
Also - over the course of yesterday, I copied the folder and it's contents more than once and placed each copy in a few different places so as to be able to try each location. Could multiple copies be the cause? If so - how do I know which to delete, and where should everything actually go?
There MUST be a solution. I've spent literally days trying to figure this out.

Take a look at O2M.
It claims to be "the fastest way to move your Windows® Outlook® email, contacts, and calendar appointments from your PC to your Macintosh® computer!" $10.00
- Wayne
PowerMac G5   Mac OS X (10.4.8)  

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