I use MS Office 2008, which works OK (mostly) in Sierra, although Word and Entourage occasionally hang up and I have to force-quit. (I don't use Excel or Powerpoint.) Entourage 2008 is my email client and I stick with it mostly because my wife knows how to use it and she doesn't like to have to learn a new program.

In the near future, I will upgrade to High Sierra. Although Roaring Apps lists Office 2008 as working fine in HS, there is only one statement to that effect. Eventually, I will not be able to use Office 2008 because Apple will switch to 64-bit compatibility only.

My main concern in changing an email client is the ease of switching between accounts. My wife and I have separate accounts, and Mail does not seem to be intuitive in doing so, although, truthfully, I haven't experimented much. I know about recommendations for Airmail but I happen to like Word and Entourage (no snide comments, please!) and will probably upgrade to Office 2016 or 365. (I have tried Pages and don't like it. Libre Office is OK but I much prefer Word.)

Does anyone have experience with Outlook in either of those incarnations of Office? Does it still switch accounts easily? Does it preserve the ability to resend and/or redirect an email?

All comments and advice will be greatly appreciated.

Then you’ll also want to know that Office 2016 Home and Student (one-time purchase) doesn’t come with Outlook, and the other options Office 365 Home and Office 365 Personal come with the monthly (or yearly) fee.

Office for Mac 2011 and earlier have reached end of support by now, meaning no official support and no updates (security or otherwise) from Microsoft, regardless of OS version. “If some part doesn’t run, consider upgrading.”

I fondly remember my Eudora days (stretched until 2011 I think), and I am still surprised that no other client has managed to fill that gap, as it had configurability on all the things that Mail.app forces certain behaviour.

MS Outlook for Mac is included with the stand-alone Office for Mac 2016 Home and Business installation.....but as already noted above it is not included in the Home and Student package.