I can't guess why you bought what may be a 6 year old app. I'm sure you had reasons but it may be tough to get this to work today as well, changes.
If I were to transfer emails and such I would instead see if Thunderbird has documented this. Once I have my information in Thunderbird I'd either keep using Thunderbird or EXPORT it in files that Outlook can use.
-> This is not an offer to duplicate the web or write another step by step. But I do see issues with choosing old versions like that. I wouldn't. My choice would be to get Thunderbird going instead. Thunderbird is now on Apple OS, Linux, Windows and more. It's just an email app but good stuff and widely documented and discussed (in Thunderbird forums.)
I don't like the Serie Mail/iCal/Carnet d'adresses from Apple, that the reason I bought Outlook 2011 for Mac.
I succeed transferring all my contacts to Outlook.
And I try now to transfer all my emails with their categories to Outlook too but I don't succeed. Would someone have good news for me and find a way to transfer all the mails with their categories from Apple Mail to Outlook 2011 for Mac ?
It would be nice and to receive a positive answer.
Thank you for your help