On windows you can choose to get feature updates with a 4 month delay if you have windows pro (set updates to "Semi-Annual Channel" instead of "Semi-Annual Channel (Targeted)", and yes microsoft are indeed terrible with naming things). I never had issues with windows updates on that branch. There is also windows enterprise long term servicing branch (LTSB), which gets feature updates every 3 years (but is meant more for things like point of sale systems, not for regular PC's).
On macOS you can stay one major release behind. So, stay on mojave until the successor to catalina is released, then upgrade to catalina. You still get security fixes and full software ecosystem support, but far fewer issues with buggy updates.
On android and iOS you don't really have good options to my knowledge.
Second the recommendation to stay on Mojave. I do this for my $WORK laptop and it still gets back-ported security updates. $WORK's IT department has advised Apple users to hold off upgrading to 10.15 and it seems they have good reason to continue dispensing that advice, still...!
Heck, I do that with my personal laptop. Feeling pretty happy having read these comments that I never took the leap to Catalina.
I feel pretty sure this must be common because I still see apps and infrastructure, even last month, coming out with updates related to Catalina compatibility.
It sucks though. I have a Google Pixel phone and never hesitate to apply updates, I even look forward to them. I don't think I've ever had an Android phone experience the sort of severe regressions that occur regularly with Apple updates.
I've been a MBP user for a long time, but I'm really starting to wonder if it's time to take a leap soon. I've been using this laptop for maybe a year and:
1. I'm scared to upgrade to the latest OS
2. The screen's coating has been damaged and has key-print impressions on it. This always happens and Apple seem incapable of fixing it.
3. The latest butterfly keyboard has at least not broken on me for 8 months or so, but the options, C and A keys have worn through and now have holes in them. This started happening a few generations ago and now seems like a regular problem that I'm just supposed to accept.
4. Very soon after getting it something happened to the metal such that it has a large discolouration on the bottom left, of a type I've never seen before. Nothing seems to fix it.
5. The screen routinely gets a yellow splotch in one of the corners if the laptop has been in my backpack for a while.
The problem is that despite not even really having improved for years, macOS is probably still the best OS out there. Linux on laptops has never worked well - my colleagues who try to use it routinely have issues with webcams not working properly. Windows laptops seem to vary wildly in quality and many of them have stupid design flaws like putting the webcam at the bottom of the screen instead of the top, coming loaded with crapware, anti-virus products that cripple performance, Windows is still a rats nest of weird problems under the hood. And their way to make it better for developers is to just bundle Linux?
I really wish there was more competition in the laptops-for-technical-people space.
FWIW I put ubuntu LTS on my thinkpad T460p and everything worked flawlessly except for the fingerprint reader. For thinkpads that seems to be the rule: everything works except for the fingerprint reader.
If you want good linux support on a laptop you need to do some research, but there are options. Thinkpads, XPS, ... They’re just not that much cheaper than a macbook if you want comparable specs.
On macOS you can stay one major release behind. So, stay on mojave until the successor to catalina is released, then upgrade to catalina. You still get security fixes and full software ecosystem support, but far fewer issues with buggy updates.
On android and iOS you don't really have good options to my knowledge.