Windows from win3 to win10: Cheap hardware, easy software setup
Linux from Debian to Fedora to Suse based: Open source, "free", nowadays good looking, largest community, missing software (Gimp is NOT Photoshop), most similar with webservers
macOS from 9 to latest X: Keep coming back to this one, best combination of the above. Easy software install, but also similar to linux, best looking but expensive hardware
UPDATE: I though the question was in the "... for development" context. In lifetime, also used these ones: Basic, MSX Ease, AmigaDOS, Amiga Workbench, MS-DOS, FreeDOS, OS/2, BeOS, FreeBSD, IRIX, ReactOS, ChromeOS
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Win95-10, mostly because I got it for free and I grew up with it. It's a good OS, however the user data handling is fairly problematic, and as a tinkerer, it becomes difficult to replace parts at some point.
macOS and iOS. Sporadically in different versions. Mostly for compiling apps for iOS. My father once had a macOS set up for general surfing, which I sometimes used. I wouldn't jail myself, though, and I don't own any Apple appliances myself - safe for an Apple Cinematic display (which is gold!!!)
Android. Not many mobile systems to choose from. Android is quite good, however there is so much Google bloat on the platform and license problems, it's becoming its own walled garden. I don't like it. I am looking forward to Purism and what they can deliver pure-Linux wise next year.
Kubuntu. Cannot remember which version, but has been a while. It's KDE on Ubuntu. It was my first Linux experience, however I never got warm with Ubuntu, so I went away from it.
Debian Linux 5-9, mostly for my web server. Debian is conservative, some would say old/outdated. However, for its use on a server, that's perfect, because it's very stable. Still powering my private servers :)
OpenSuse Linux. We had to use it at University. It's quite nice, however at the time I was all about Arch Linux, so Suse felt a like a step back tinker-wise.
FreeBSD 9 and 11. I love a lot of parts of FreeBSD, however my server hoster does not support it as OS and I can't really use it on my desktop, because the drivers are not up2date enough for my gaming and dev purposes.
RHEL. We use it on servers at work, so I have to use it from time to time. I think it is very similar to Debian. No surprises, rock solid, runs forever, BORING. And that's a good thing ;)
Nexenta, Illumos, OmniOS. Powering my NAS. Nothing better than running the full force of Unix on a storage. I thought about using a BSD, however the tooling for the Unix systems is better. By the way, at the moment, my OmniOS NAS sits on top of an ESXi, which allows me to add more servers to my home network. Keeping disk access speed is a little tricky to setup, but once it works, nothing can stop it :)
Arch Linux. It's fairly easy to setup for being so low-level. It's also very bleeding-edge and working with it requires some Arch-knowledge. I'd have continued using it, but I found Gentoo to be more to my liking.
Gentoo Linux (rolling, since a few years). It is highly influenced by FreeBSD and allows for a very great level of optimization and tailoring software to my personal system (by compiling everything myself). The degree of automation is ok, which is a boon, though not as good as with an integrated system, like a BSD would have delivered it. It's my desktop system of choice, however it is a great deal to set up and even a greater deal to set up correctly. Once running, though, the system can be optimized at any time in any direction and mostly just works. I heard of Gentoo installations which are 10+ years old on desktop machines, surviving hardware-generations. Awesome!
KaOS Linux (rolling). If anyone wants to know the best modern desktop Linux (system? Who says it must be a Windows or macOS anyway?) for a normal user (surfing, casual gaming, light office work), I'd recommend them KaOS any day. It's super easy to setup and maintain, since they use a GUI for the regular tasks. Being entirely focused on KDE and optimizing everything for it, it is beautiful and feels like an integrated system rather than a mix of hundreds of individual packages. I use it to keep my old laptop with Nehalem i3 alive. Good stuff!
Redox. I dream of creating my own Redox distribution, focused on Desktop usage, gaming and dev. At the moment, one can be happy if Redox runs on hardware at all, however it's getting better day by day.
I'm pretty sure that I forgot one or another system above, however they are not important to me anyway. In the future, I'd like to try Haiku at some point, it looks nice for general usage. Also Google's Fuchsia OS might also be quite interesting, so I will at some point try to get my hands on that.
CP/M, TRS-DOS, NEWDOS80, PRODOS, DROSSDOS, OS/9, Xenix, MS-DOS (well, duh), Atari TOS, Amiga Workbench, Oberon, MACOS 1 through 9, OSX, OS/2, Windows (pretty much every version ever), BeOS, QNX, Solaris, FreeBSD, Haiku, ReactOS, and of course the endless stream of Linux distro's each (as a desktop OS) more crippled than the last.
Not to mention all the various ROM BASIC's that also did double duty as the disk operating system, such as on the Commodore 64 or TRS-80 Coco; a system that often made me wonder why we even needed a "DOS" on early computers given that making the "command line" also be a BASIC interpreter in ROM generally worked just as well... putting even modern shell scripting to shame. Even back on the Trash-80 model 1 I kept asking why we needed the 18k+ memory footprint that's not even as capable as the 12k Level II ROM built into the machine. Don't even get me STARTED about MS-DOS' footprint and how you needed a 128k machine to even use it "well".
Overall though I'm an OS whore; there are dozens more I didn't list as I can't remember all of them.
- windows msdos - windows 10
- Novel NetWare
- linux ubuntu, arch, suse, debian, fedora, centos
- macOS - macOSX
these are the ones I was sentient enough to actually use
I still have my dual boot where I use arch with windows 10. I am a classic linux user, although I try to use and understand every system, I made my choice :)