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How have MS Paint, Notepad and the Command Prompt not been updated for 20 years? I can only assume they are some kind of running joke at Microsoft.
The Console Host has seen a bunch of interesting incremental improvements over the course of Windows 10 as well. The Anniversary Update, especially, included a bunch of ConHost updates too, in particular a number of things inspired from Bash On Ubuntu On Windows needs like deeper console emulation stuff (revenge of ANSI, *nix terminal emulation, etc).
I'm pretty sure that Paint has seen some improvements in the past 20 years. At least it supports .png's and other image formats. I rarely use Windows, but when I need to upload screenshots, I use print screen and paste to Paint for saving to a file.

Don't fix it if it ain't broken, I guess. They did actually update the Windows Calculator in Win10 and completely broke it. It's only got a handful of features it used to and seems to use floating point arithmetic so you don't always get correct results. It looks pretty and consistent with Win10 apps, perhaps it's more important than actually calculating.

Trying out Raymond's suggestion[½] to test arithmetic precision (1 / 3 * 10000000000 - 3333333333 =. The result is one third exactly. Type 1/x - 3 = and you get zero back) yields the exact result with calc on Windows 10. It's definitely not standard floating-point.

[½] from here: https://blogs.msdn.microsoft.com/oldnewthing/20040525-00/?p=...

Must have been something else but I recall a big fuss over incorrect results from calc.exe when Win10 came out.

It's still inferior to the old calculator even if it has been fixed to give correct results.

I use Greenshot (FOSS: http://getgreenshot.org/) for screenshots as it has a built-in editor/annotator and can also throw the images straight into apps or upload them to various repos/tools.
I don't bother installing any 3rd party apps on Windows. I use it for gaming and some proprietary apps (SketchUp, etc) not available on Linux.

Paint is more than good enough for saving clipboard contents to a .PNG for uploading.

Snipping Tool is a built-in program in every Windows since Vista. It's a much nicer tool for taking screenshots. Supports screenshotting individual windows or rectangular clips, and will easily save directly to a file or even send to your email program. Some basic annotation support, too.
As for Notepad: https://blogs.msdn.microsoft.com/oldnewthing/20040525-00/?p=...

Paint got a significant overhaul with Windows 7 and somewhere in between it got the ability to save/load PNG, GIF and JPEG.

Command Prompt got a significant overhaul in Vista, which broke drag & drop of files as collateral damage, which was subsequently fixed in Windows 7 again.

Which all comes back to what Raymond notes in that blog entry: If you change how things work underneath no one notices. Heck, even if you change how things look on the outside no one notices, apparently. Paint 20 years ago looked and worked very differently from now.

This is just a great reminder that OS X doesn't come with any sort of image tool at all. Unless you consider "Preview" an image tool because it allows crop and resize. Come on Apple, throw us a bone.
This probably will have something to do with hololens. The whole ui will translate nicely over to hololens.
Of course it's tightly integrated with your Microsoft account! I wonder if you'll even be able to use it without one?

It's probably a UWP app too. Yuck! I hate what Windows is turning into.

I haven't been using Windows significantly in some time. Is Paint.NET still around? It is what I would point a user to, if they aren't going to e.g. need/pay for Adobe or the like.