I can't speak to LittleMachines company policy, but I can describe my successful use of Outlook2Mac for a client, to convert some 400 megs of Outlook 2003 PST data to Mac OS X mbox format. I then imported that into Apple Mail (Jaguar, 10.2.8, which is what my client is using). The ultimate goal is Eudora 6.2.3, but Eudora fails (crashes) on attempting to import the mbox files produced by O2M directly. Notably, however, it also fails to import mbox files after they've been converted to Apple Mail--makes me think the Eudora 6.2.3 importer isn't perfect.
Back to importing to Apple Mail (under 10.2.8): Of the ~25 mail folders, 5 were not imported correctly by Apple Mail under Jaguar--only 1 message came through in each case, instead of 1013, 408, 522, 679, and 584, respectively.
Not one to give up easily, I tried importing these problem files into Apple Mail 1.3.11 (v622) under Panther (10.3.9). Success! All messages with their attachments were imported. You can stick with Apple Mail if you like, but I much prefer Eudora--more robust. Keep reading if you want to use Eudora...
In Eudora 6.2.3: File, Import Mail, then choose the Apple Mail option (default). Select Local Mailboxes, then click the bottom left button in the importer window. I chose to import only "mailboxes, messages and attahments". Eudora chugged along for a while, finally leaving me with a new mailbox folder tree for the imported stuff, which came in unscathed.
Upshot: Outlook2Mac worked for me, and a reasonably straightforward conversion. Off to try bringing that 125 MB mailbox and the others into Eudora at my client's under Jaguar...
One other note: keep Eudora mailboxes small--say in the vicinity of 5 megs. They can become corrupted when they get too big.