When was the last time you installed your own drivers on a desktop Linux system, and for what?

2018, for keyboard and touchpad support on a 2016 MacBook Pro. (That driver was eventually upstreamed, but wasn't at the time.)

But I guess that's kinda in-line with this thread, that Macs are a pain to run Linux on.

I don't remember installing any drivers in Linux in last... I don't even know how many... years. For the hardware I happened to use, it was Mac-like experience.

And actually, Windows 10 is also approaching this state, but it is not there yet.

The great thing about Linux is that almost every driver is included with the kernel itself, so you don't need to worry about installing drivers. Of course, there are vendors who don't like to cooperate with Linux developers, and release kernel-tainting drivers outside of the mainline kernel.

I last installed drivers on Linux... in 2007? 2008?

I last installed drivers on Windows late last year.

I've had to on Linux for a very common wireless networking chip. Also for a scanner from a very common printer brand (that ironically has excellent support for printers on Linux). And this is Debian on a ThinkPad--a very common combination. Almost as good as Windows but given I had to load my wireless drivers via USB I still consider Windows the gold standard when it comes to built in drivers. It at least does well with networking drivers which is the most important and essential drivers to have. Everything else windows can easily download and install automatically over the network. I last did a manual install for drivers on Windows years ago cos it just does it by itself now.

Hm? Debian is famous for not including nonfree wireless firmware on purpose (drivers are an entirely different thing). They also provide an optional installer with these included.

So your example seems to be completely unrelated to the question.