But ... patching.
When I was first reading your comment I assumed it was experience in the distant past. The different experiences people have with the same software is incredible to me. I have owned four Windows computers, up to present day, and maintained those of family and some friends, and not once have I had to reinstall Windows since the days of Windows 2000, excepting harddrive failures. I always wonder what makes the difference.
But I guess if I knew, Microsoft would know (being staffed by people smarter and more informed than me), and hopefully fix whatever causes the problems necessitating reinstall.
It's like all the complaints about Firefox's memory usage - people have complained about it for years, it's clearly a real problem for some? many? users, but I have never seen it on any platform.
To give you a real life example, just last week I was trying to get my Win10 laptop to do local DNS lookups successfully. (I run dnsmasq on my home LAN, and I have it resolve names like "router" or "server" or whatever.) Not a problem on Linux or MacOS, but on Windows it's often a problem. Why? I don't know. There are all kinds of different ways Windows looks up names -- NetBIOS, WINS, DNS, etc., and they interact unpredictably from where I sit. I'm not the only one with this problem so I found a lot of blog and Stackoverflow posts with various fixes. I applied one of them by adding "." to the end of all local lookups. Seemed to work just fine.
Two nights ago it stopped working. Then I rebooted. That made it work again. Last night it stopped working. I rebooted. Nope. Local DNS is no more.
Why? I have no clue. So I'll just go try some other random fix to see if it works.
This process of applying random fixes should seem familiar to anybody who troubleshoots black boxes. I really don't want my OS to be this much of a black box.
If you're interested in avoiding that, try a rolling-release distro (updating frequently) with good documentation and a sane low-level setup.
I've heard good things about OpenSUSE Tumbleweed, but I have never tried it, so I can't vouch for it.
If you have the time and energy, I'd recommend you to look at a couple of distros yourself and see how much of the "dirty hands" part you can grasp yourself from the documentation. Can you fix GRUB or their equivalent yourself? Is there documentation on how to do things without a GUI? I'd say those are certainly a good sign.
As a bad example, I wasted a whole afternoon once trying to uninstall a botched Radeon driver in the TTY on Fedora (since it screwed up Xorg beyond repair). Their documentation was abysmal[1]. That's the stuff you want to avoid.
[1]: In fact, in the end, it turned out I had to set a magical environment variable that was never mentioned in the small paragraph there was in the docs. Oh, and of course, the driver was botched because of a system upgrade I couldn't revert.
Edit: OTOH, if you're more patient than me (and don't screw around with e.g. PPAs because you want a new-ish version of certain libraries), you might find using ZFS for your main drive to be a good idea. Make a snapshot, upgrade and if something breaks: revert and wait for a fix.
Edit2: Also, if you're going to try a rolling release: Don't wait too long for updates and find the news channel where breaking changes (and the necessary upgrade steps) are communicated. It's important to know about those, and it simultaneously helps you in guessing how often they're about to happen. Arch's feed is on their landing page, for example.
Linux: 0 MacOS X: 1 Windows: Lost count a long time ago. Had to do it twice with Windows 10 in the last year.
Have you ever noticed how in most orgs, every IT guy's first response to a weird-looking Windows problem is to suggest a reinstall? And that's not even irrational. Troubleshooting Windows takes too long to be worthwhile, because there are too many places to look for where things might be going wrong. Its complexity has become unfathomable to mere mortals, and it shows in maintaining the OS.