I currently use Outlook 2016 (with .pst files storing my data, not IMAP), my Calendar within Outlook is my iCloud Calendar, which syncs to my Phone and iPad. When I'm not at my computer, I can't see the emails that I have put colored categories on for follow-up, or see the folders where I have stored all my emails . And I worry about the .pst file crashing, but at the same time I don't want to move to IMAP because once you delete something it is gone for good.

What "setup" would allow me to see my contacts, calendars, and emails THE SAME WAY across all Windows and Apple devices so I can manage them all wherever I am?To be honest, when you are working with multiple devices, IMAP is REALLY the only practical option. Sure when you delete emails, it will delete from all devices but your mail server will more than likely offer some sort of trash or deleted items folder for this purpose. You can ALSO export your PST file from Outlook when you are using IMAP if you are really concerned and want to keep a backup of all your emails.Perhaps you should switch to a webmail solution such as gmail. I think that is one solution to making email behave nicely across multiple devices.

Note: I do not have any Apple devices. I have an Android phone and an Android tablet, in addition to PC's running Windows.