So here is my real life experience doing what you need to do:
1. you can import a .pst file in to outlook 2011 for mac; I did it three times and had thousands of corrupted emails each time.
2. If you load your .pst file in to a windows version of outlook, then drag all of the emails to a gmail account set up using imap, then set up the gmail account on your mac, you can then be certain all of your .pst data will be there and not be corrupted. I had over 22,000 emails to transfer and failed to get good data three times with outlook for mac, but succeeded on the first try using the transfer to gmail using imap.
good luck, PM me if you need more help; I am just finishing up this process now on my end.