Thinking about just giving everyone Macbooks instead of O-365? Think again. The Mac client is similarly limited vs the classic Windows fat client. Microsoft is balancing on a knife edge because if the non-Windows fat clients and O-365 had feature parity, there would be no compelling reason for many to run Windows. Unfortunately the user community is caught in the middle.

Even so to address the original question - it's been my personal experience that moving docs between MS users and LibreOffice also exposes lots of funny formatting issues, particularly in Word docs. If you're not exchanging docs with others that's one thing, but IMHO you don't want to submit your resume or any equally important document written in LibreOffice format even in compatibility mode. Better to print to PDF.

The Microsoft E-mail client is an absolute shitshow. It's another huge regression in the Office suite.

I got new computers for my parents and made the mistake of getting them Windows machines because that's what they're familiar with. I set up Office, but Outlook is so defective that it was literally unusable. The final straw was that it defies Windows's own system-wide font-size setting. I needed to make the font bigger so my mom could read it, but Outlook ignored it... leaving her In box totally illegible to her (and barely legible period).

I was pleasantly surprised when I installed Thunderbird (after not trying it for 20 years) and everything worked well. It even handled the 15,000+ messages in her AOL In-box (yep, AOL).

Beyond the E-mail issue, Outlook 365 continually stopped working and badgered both my parents for MY account credentials, so I shitcanned it and replaced it with LibreOffice... on my systems as well. I find it less reprehensible than Office.

It depends on the user and how they use Outlook. Microsoft’s tools for managing email are hot garbage for folks who get alot of mail.

But… many folks don’t understand how to use GMail effectively with things like labels, and Google lacks alot of the things that users rely on. (Drag and drop of messages into messages, folder structure, lack of message view, etc)

Unless you have a know how to be a good Gmail user, you’re gonna miss messsages.

In the long run, Outlook is in the middle of a long re-engineering process and will probably be better for it. Google definitely underinvests in their products… perhaps the webifying of Outlook will drive change there.