I have recently bought a new Mac. It is running Office for mac 2011, Home and Business including Outlook version 14.3.6. 

My old G4 computer is running Office 2004 and its mail application is Entourage for mac 2004 version 11.4.0. I have tried to transfer my old emails to the new mac by using 'File Export' and exporting Microsoft User Data from the old mac document folder to an external hard drive. I have then used 'Import' to get this data from the external drive to the new mac - while my 2004 Microsoft User Data has been imported from the external storage including my Office 2004 identities, my old emails have not appeared in the new Outlook's window. How can I get these mail messages into Outlook on the new Imac?
I have downloaded Office 2011 as a trial and outlook to import my lost entourage emails when I upgraded to Lion. The import started and I have some emails, but not my recent history. Outlook now quits and says there is an error when I try to restart the import.

1. Is Outlook (in Office 20l1) more robust and does its design avoid potential for lost data. Can an import of existing data (from Entourage 2004) be accomplished reliably? 

2. What other feature differences are there between Entourage 2004 and Outlook 2011?
I switched from Entourage 2004 to Outlook 2011 and can no longer send mass emails. My outgoing mail server says there is no limit on my account and I never had a problem with mass emails before the switch. I tried switching ports, outgoing mail servers, but since the problem only started when I switched to Outlook, it seems there may be a setting or a workflow I am not aware of. I send out a newsletter every 2 weeks to 2500 recipients and can only send in batches of 25 at a time.
Help!
Yesterday I upgraded my MAC OS from 10.6.8 to Mountain Lion.  When I did this,  it disallowed access to all my emails that were on Entourage 2008 since it won't support Power PC programs.  Someone suggested I then up-grade to MSOffice 2011.  I got the trial offer to see how it works.   When I tried to import my data,  it would only import from Entourage 2004,  but not Entourage 2008.   When I go to import,  it indicates that it has indeed found the Files in my user Files,  but below -- where I'm supposed to highlight it and import -- it says  NO Entourage files are found.   Don't know what to do now and I can't seem to get any live help.  Please prove to me that there is a live person at the end of this....