Despite that, Windows is easily one of the least annoying OSes that I have to deal with.
I wish I could run it on my phone.
Instead I either have to accept the walled gardens where there is zero transparency or spend all my time hacking my phone to give me the same kinds of freedoms that I enjoy on Windows.
Considering how annoying Windows 10 can be (scheduled reboot which you then can't disable, update downloading in the background without asking and at the most annoying of time, impossible to disable telemetry), I feel sorry that you use OSes which are actually worth.
It was painful as hell to develop for Windows Phone. You had to use Windows on the laptop you were developing on, and go through licensing crap for that. Then you had to install Visual Studio, and then some weird addon to that. They were losing developers at every stage of this process, and would never admit that the process was a pain or try to simplify it. (My guess is that all three of these were handled by different departments at Microsoft who were forced to integrate with each other's products).
So in my opinion, it has nothing to do with anti-Microsoft culture, but more to do with the fact that Microsoft was too arrogant to realize that they were the underdog in this race by a significant margin.
MS really could have owned that market. ActiveSync made sure they didn't. They were a good 3-4 years ahead of everyone else tech wise. However, their dev stack was awful and full of gotchas. Apple and Google imploded that and made it easy to dev for. Their crazy BOM build system was a fork of visual studio 6 which was cobbled together with CMD scripts. Then on top of that the OS arch was different than pretty much anything else. There were some seriously bad spots where if you used the wrong system dll you could crash the box. Oh you need a new firmware to fix that good luck as there is no built in firmware update on your box. Have fun spending 2 months getting that patched firmware out of the company too.
Your guess about different depts is almost right. They also outsourced portions of it. Some parts were internal. The licencing around it was byzantine. Also portability was shoddy. That was due to the MIPS/ARM ISA environment. Every phone was slightly different from each other (you can see similar issues today with ARM dev boards). x86 did not end up there as IBM compat was king and if you didnt have that no one bought your board, ARM/MIPS do not have that type of market force. You had to in some cases ship an executable for each phone. Then on top of that the phone carriers wanted to charge 40-50 dollars per megabyte sent/recv.
WincCE, WinCE, you cannot be serious. WinCE was produced as a response to the ‘Palm Pilot’. WinCE ran on a “Palm PC”, not to be confused with the “Palm Pilot”. Palm sued and Microsoft renamed it to "Palm-sized PC" or the ‘Palm PC’. MS really could have owned the market with the TRON real-time operating. Microsoft did joint the TRON consortium and then lobbied to have it excluded from the North American market.
https://www.itprotoday.com/windows-78/microsoft-settles-palm...
https://en.wikipedia.org/wiki/TRON_project
http://tronweb.super-nova.co.jp/microsoftjoinst-engineforum....
And secondly, remember what I said around being the underdog. Apple had first mover advantage in this field, they could afford to make their tools a little more annoying and still have developers sign up. Microsoft was the underdog, they should have given away a free copy of Windows with all the Visual Studio crap preloaded to developers; that would have gone a long way towards getting developer mindshare. But that would not have made sense to the revenue obsessed execs at Microsoft, and so did not happen.