As a point of fact Mac Outlook Indeed is an intricate E-mail application and one certainly can face the difficulty using the same. So I would say moving Mac to Windows is a better option and for that you can get hold of a list of utilities online. One that I am very much familiar to is Outlook Mac Exporter as this will let you convert your OLM file into PST, EML and MSG file.
Check this out: - http://www.securasecurity.org/tag/olm-pst/