01189998819991197253 , 9 hours ago

1. I use rhythmbox, but my usecase isn’t quite as extensive as yours. I don’t think it has smart playlist capabilities, for example. But it is able to rip MP3s from CDAs, which is cool.
2. I haven’t found anything that will work 100% with iphones on Linux, but I no longer have iphones, so it’s been a while since I’ve looked.
3. MS Office used to work fine enough under WINE. I’ve had 0 luck with 365. There’s LibreOffice, which is a great replacement for most things Office (minus Outlook). Thunderbird, I think, has an exchange plug-in. On my home computer, though, I use Outlook web, which has worked just as well as Desktop for my use cases so far. I understand you want Desktop Outlook, so this may be a deal breaker. However, Desktop Outlook New is heading towards WPA anyway, and MS is trying to sync the functionality between desktop and web, so this may only be an issue for a little while.
4. I don’t have this use case for my computer, so I can’t really help here. But others on this thread seemed to have provided some nice options.
5. not sure you’ll get integration into proprietary software like Evernote, but there are built-in scanning tools that “just work” with every scanner I’ve thrown at it thus far. I do not have the same scanner you do, though.

I recommend grabbing a live ISO of a distro you’re interested in trying (Mint seems to just work for most people, ElementaryOS if you want to maintain that macos look/feel), and just trying it out on RAM. No installation needed, and you can get a better feel if this will work for you. Don’t expect a perfect fit, though. Workflows and solutions will differ from Mac to Linux, just as they do from Mac to Windows. This was one of my reservations, and why I kept finding myself back on Windows and Mac. The end goal, IMO, should be to get out of the walled garden in which you’ve found yourself. Once I realized that, once I switched my goal from ‘finding exact replacements’ to ‘getting out’, switching was much easier and smoother. Good luck! Post any questions you have, and we’ll do our best to guide you right. This is a great and super helpful community (mostly lol).