Interesting that my experience with Mac and Windows has been completely the opposite. I owned 2 PowerPC Macs which went the way of the dodo and I had to replace hardware AND software to run on Intel. So running my old Final Cut Pro and Adobe suite was not possible on new hardware.
Compare to Windows, I am able to continue running very old software without having to upgrade them. OSX is not free (as in freedom). You can't legitimately virtualise it on non Apple hardware, yet running Windows on Mac hardware is very straight forward.
If I had to pick a platform for web projects though, I'd actually pick Ubuntu. It's very easy to automate.
Macs are about the package, not the computer or the OS alone. You get a beautiful, well built machine with an OS to match. The OS is not terribly alien and, if you are a serious developer, it has enough Unix to make you happy. Unless you look too closely (I spend most of my time with Python) it looks a lot like the servers that'll run your code.
Ubuntu is my preferred OS for work. Matching the servers my code runs on is great, even though I run my code inside VMs or containers (often with the last LTS release). As you mention, it's exquisitely automatable - I can do and redo configurations in seconds.
Compare to Windows, I am able to continue running very old software without having to upgrade them. OSX is not free (as in freedom). You can't legitimately virtualise it on non Apple hardware, yet running Windows on Mac hardware is very straight forward.
If I had to pick a platform for web projects though, I'd actually pick Ubuntu. It's very easy to automate.