Configuring a printer is pretty good, actually: for the most part, you plug it in, and it Just Works™. Networked printers are another matter, but by no meand impossible.
Presentation on Linux can be handled by LibreOffice, Google Slides, or Reveal.js (which has become increasingly popular with developers of late)
I've never had trouble with updating my system, and I'm on ArchLinux. The one thing you may have trouble with is wifi, but if your wifi chip's supported, the rest is most likely good. However, it does depend on your setup.
Really, the only thing you might have trouble with is video editing, and even that's not so bad anymore: OpenShot is as good as WMM ever was, and Lightworks, the NLE of choice for many professionals, has a Linux version.
As for gaming, I've been gaming on linux since 2011, when Steam on Linux was but a madman's dream. It was possible to play many exellent games (some through wine, some native), and with the dawn of Steam on Linux, that's never been more true.
Spotify, Photoshop, Sketch, Illustrator, iMessage, Apple Numbers (I'd settle for Excel), Keynote (far superior to Powerpoint), Hearthstone, Apple Calendar, Apple Mail, Apple Maps, Apple Photos
For nearly every one of those apps I'd have to settle for an inferior user experience on Linux. It would be significantly more bearable on Windows, but still would be a UX compromise compared to my experience on the Mac today.
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.
Nope. They (Skype/Microsoft) have not updated skype in years. It's still version 4.3, and recently on Linux Groupcall is problematic as all the other Skype clients got upgrades.
Though digging around for a known workaround to that last problem it appears there is a new alpha-grade update for Skype-on-Linux: https://community.skype.com/t5/Linux/Skype-for-Linux-Alpha-a...
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.
For presentation software: personally I've completely switched to HTML5 based presentations (with reveal.js generated from markdown with pandoc), because even in 2016 I still see professionals at big conferences fail at playing back videos, or just plain hanging their Windows computers, when using PowerPoint. But when was the last time a video failed to play in your browser?
I have no idea at all if that would be remotely close to suitable for you, but, y'know, have a random data point in case it turns out to be helpful.
So, for me, as far as I can tell, "don't use IE" plus "don't install random crap you downloaded from the internet" plus "my mail client is mutt under screen on a server" between them are basically sufficient defense these days. How far that generalises I can't really say.