In your case the problem I see is that you are using a lot products from Apple. In my case is just Keynote, otherwise I'm using just the OS itself, and I even have an Android phone, so the switch could be simpler. Unfortunately I think you'll require to do researches for each single software in order to potentially migrate to something else. The good thing is that for almost everything there is some indie solution that is great, but the bad thing is that it's not as simple as just sitting and letting Apple provide good integrated solutions. For iMessage however I would go towards Whatsapp, it's going to happen anyway world-wide IMHO, it's just North America that is using Apple messaging mostly. I totally agree it is significantly simpler to switch to Windows + VM or Windows in dual boot than bare Linux.

Photoshop, Illustrator, Spotify, Excel, and Hearthstone (more or less) work well through Wine. I've never heard of Sketch, so I wouldn't know about that.

iMessage and Apple Maps are accessible from your phone (as is Hearthstone, for that matter), and probably more convenient there, although iMessage might be useful on the desktop as well. Google Maps, however, is a thing, and probably better.

I've heard good things about Shotwell for photos. Have you tried it, or did you dismiss it out of hand?

Mail and Calendar can be replaced by Thunderbird, or any number of other email clients if Thunderbird concerns you. None of them, AFAICT, are worse than Apple's mail and calendar apps, which are pretty "meh" IMHO.

So of the apps you listed, only iMessage, Keynote, and Sketch don't work on Linux, and don't have viable alternatives.

Alpha do not work very well. You still can install old 4.3 version, work better than new version under Win 10.

Skype need to be some kind of amazing mismanagement where with such simple product they keep losing quality. To compare Curse/Discord for games work and look way better.