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.
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.
[½] from here: https://blogs.msdn.microsoft.com/oldnewthing/20040525-00/?p=...
It's still inferior to the old calculator even if it has been fixed to give correct results.
Paint is more than good enough for saving clipboard contents to a .PNG for uploading.