There are many good hardware choices at this point in order to replace a Macbook. What is entirely not clear is what software to use to replace a Macbook.
I'm just too invested in macOS in terms of apps, comfortableness, muscle memory, etc. I actually really like it as well.
I never thought I'd compare new Apple hardware versus Thinkpads to a presidential election, but here we are.
Aside from a Hackintosh my only choice is a maxed out 2015 one that should last me about five years, if not more, with my current usage. It's not the choice I wanted to make but I'm not getting a $2000+ laptop without any ports I can use without adapters.
Your real switching cost, however, is in your apps. If you're dependent on something that is Mac only, it is really, really hard to switch.
Most of my core apps are multiplatform (Sublime, Slack, 1Password, Evernote etc.) but I was concerned about Terminal and Aperture. Terminal was easily addressed by Cmder (and now you can use Window's Linux shell instead), and Apple EOL'ed Aperture, which meant I had to find a new RAW tool (I use DxO Optics Pro now, which is cross platform).
I just did this.
I currently use a second-from-last generation 11" Macbook air and it works perfectly and I expect it to last another 2-3 years.
However, I just purchased a refurbished latest-generation 11" macbook air, with maximum specs, to keep on reserve.
Now I can put off these decisions for 5 or more years.
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?
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.
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.
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.
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.
I do use Jessie with Broadwell, and it runs quite well indeed.
Gnome 3 is a full desktop environment with pretty good tiling functionality built in and enabled by default.
That might be too hard, but, if the cloud paradigm is totally unrealistic, then you do get an escape key plus you can run an LTS version of Ubuntu in a browser tab. Here you can run a dev stack, do work in real spreadsheets and run terminal windows for vi. Okay, no Adobe or other professional software but you do have Android apps.
There are two options for Chromebook hardware. Much like how there is 0, 1 and infinity with everything pretty much in-between, for maximum Chromebook chic go for either the ultra high end Pixel or the ultra low end machines that cost less than anything else. Anything in-between is a compromise on minimalist stupidity. The bargain Chromebooks are designed for 9 year old kids and seem not to contain things like CPUs, RAM or other storagey stuff. They are indestructible and the battery lifetime is measured in days when in realistic usage, just charge them overnight once in a while.
With either hardware route you can install a full cornucopia of operating systems in an Ubuntu chroot with Crouton, to have your 'Unity' desktop in a tab. Here there is an escape key for working in vi.
Just for added operating system overhead and complexity you can run virtualbox in your Ubuntu chroot, then you can run Windows 10, Ubuntu and ChromeOS fully side by side. I have no idea if Hackintosh is possible on a Chromebook but that sounds like a bit too far.
The Chromebooks are definitely RAM limited and ports are ancient history. However, if you go high end Chromebook Pixel LS to run the above stack then you do get the finest keyboard, 3:2 screen, aluminium case, sound system and browsing experience going. Nice hardware but a heap of operating system hacks to run useful software.
1. Run Windows 10 and Linux in multi boot, use Linux normally, Windows when you need stuff that are not available on Linux.
2. Run Windows and use VMs to have a Linux development environment.
3. Run Windows with some Unix-alike layer, like the one introduced in Windows 10 or something.
I think for me it's "1", I don't think I'll be able to use Windows on a daily basis, since I still see people that install things like anti-malware/virus. I can't go back 15 years in computing experience easily.
P.S. Note how people that need to develop for Apple devices, like mobile devs, don't have any way out of the Apple ecosystem, since the SDKs are Macos-only.