I would suggest you OLM to Gmail converter tool which is very Effective software Transfer Outlook Mac to Windows. If you are going to perform manual solution then keep backup of your data because the solution is less secure and there are chance of data loss as well. On the other hand, if you are choosing an expert solution then I would say you try the demo version to have an idea about the utility.[table][tr] [td]
https://www.kdetools.com/olm/gmail/[/td][/tr][/table]