The state of switching to Windows from Mac in 2019

Same thing here. Sold my 2013 MBP and bought a Thinkpad X1 carbon. After a year of frustration, bought a used 2013 MBP.

Windows is somehow worse than it used to be. There's two control centers for some reason. Much more notifications and intrusiveness. Taskbar auto-hide doesn't work consistently. Updates install without permission. The big thing is the apps. Apps are getting much less functional (just like how the Settings app does a fraction of what Control Center used to do.) OneNote is a great example: the UWP version lost so much functionality compared to ON 2016, but the latter has been abandoned.

Weirdly enough, I never found a good PDF viewer. Acrobat DC is a slow and a battery hog. Edge/Chrome are non-functional (don't handle search properly on many PDFs). Many alternatives are .NET based on battery hogs. Moreover, since Edge/Chrome won't let you use a PDF plugin anymore, the workflow is completely broken. (Download the PDF then open it in a separate app.) I never thought that Preview would be the "must have" Mac app.

Oh, and the trackpad! RDP from a Mac into a Windows terminal server is a better mousing/scrolling experience than native windows on the X1 (which has an MS Precision touchpad).

Oh, and power management was real hit-and-miss. Sometimes I'd get a full 10 hours, and sometimes, under the same workload, it'd be like 6. The synaptics touchpad comes with a driver (even though it's supposed to be an MS Precision touchpad) that had some helper utility that would randomly go crazy. (If you killed it, it would restart automatically. Deleting the binary fixed that, and had no discernable affect on mouse behavior.)

My environment requires mostly access to several Windows Remote Desktop Servers and VDIs.

Curiously I use a Mac to access them because the Microsoft Remote Desktop for Mac has some niceties such as opening each RDP session in a new Mac Desktop and best of all I can very conveniently navigate from RDP session to RDP session with a Mac hotkey.

With Windows Microsoft Remote Desktop the whole RDP session switching experience is pretty cumbersome.

So I do all programming and LOB apps use on Windows RDP sessions.

On Mac only Internet browsing and RDP session management via Microsoft Remote Desktop.

So my iMacs are mostly thin clients.

I'm in a similar situation, but I'm pretty sure that when my 2015 MacBook Pro dies, I will still be unable to find a Windows notebook with a comparable touchpad. Running Windows on my gaming desktop is tolerable, subject to the caveats you've outlined. But even with great software, Windows notebooks are still handicapped by poor hardware interfaces. I realized recently when I got a new Windows notebook for work that touchscreens exist and are popular on Windows notebooks because they partially compensate for the horrible touchpads. On my MacBook Pro, I still feel no need to augment the touchpad with a touchscreen.

I'm not sure it makes sense to point to certain hardware flaws as a reason to avoid Macs.

These are bad things (especially the keyboard switch issue, which is greatly compounded by the issue of the keyboard being a very heavy-weight repair) but... where's the manufacturer without problems?

I think what you're looking for is a manufacturer with a relatively decent reliability record and a record of "making things right" when they do go wrong. I'm really not sure of the best way to measure that, though Apple seems to consistently do well on various user satisfaction and reliability surveys.

It's cheap but crippling.