Heck, I could run my own mail server if I wanted (been there, don't want to go there again, but could if I really HAD to).
Of course, I only have one account ([email protected]) and therefore didn't have to deal with setting up multiple users, migrating data etc. I also set up 2FA for my account.
I did all this over one weekend (from looking at different providers, to signing up for O365, configuring etc), and haven't had to touch anything since. The only question I had was related to billing (I went from a month-to-month to a yearly account) and that was answered quickly by a real human being.
One time I had a question, I was able to use the web interface to request support, and a real human called me back in 10 minutes. It wasn't a very complex question, so I can't say if he was super knowledgeable, but he certainly seemed like he knew the platform, and was able to answer my question in just a few minutes.
Oh, and I know this is a throwaway account, but I'm not a shill for MS. This is just my personal experience with O365, and YMMV - it's worked well enough for me.