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.
OS 10.15.3, iMac Retina 5K 27-inch, late 2014, 3.5 GHz Intel Core i5, 1 TB fusion drive, 16 GB RAM, Epson SureColor P600, Photoshop CC, Lightroom CC, MS Office 365