HiRegarding Mails you can take help online IMAP tools, for the address book stuff, you can prefer converting them to.vcf files. Outlook windows does support vcf files. For the calendar, convert them to.icf files. Try these, only if you have enough time to deal with. My friend had tried this and it took almost 3 hours. I took help of OLM TO PST CONVERTER ULTIMATE tool by Gladwev.
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To backup and restore Outlook 2016 for Mac are easy now. EaseUS software provides effective & secure methods for great Mac users to effortlessly backup and restore lost Outlook 2016 files from Mac. Download for Mac Download for PC.
It transferred all my mails from mac outlook to windows in a max of 10 minutes. Hope it helps. Mark it as answer, if it works for you Thank you.