General stuff
Not free as in freedom
Not free as in free beer
Market share of 90+% only because of illegal vendor deals in the late 80s and throughout the 90s
Market share is only kept because "it's established now" and not because it's a good OS
Microsoft actively tries to "embrace, extend, extinguish" other OSes, applications and services
Older, but still "supported" versions don't receive feature upgrades (drivers, DX12, etc.)
Privacy
Spies on its users
Tries to trick users into creating an online Microsoft account
Gathers telemetry data even if you "deactivate" it in the settings menu
Every app that comes with a standard install has telemetry built into it
Start menu and Windows Explorer include ads
Microsoft has published usage statistics of Edge and other MS apps
They performed intrusive tactics to make people "upgrade" their old systems to Windows 10
Speed, stability and reliability
Slower in almost every task compared to Linux and various BSDs (hence its irrelevance for servers)
Severe flaws in CPU and I/O scheduling
Blue screens much more common than Linux kernel panics
Crashed/frozen applications can often tear down the whole system
No separation between desktop, window management, file browser and file picker (explorer.exe)
Installation
No live environment
Needs to reboot several times during its slow installation
Doesn't come with all necessary drivers out of the box
A bare-bone install takes several dozens of GiBs of storage
Wipes the EFI partition and bootloaders of other OSes
Applications
Comes with "modern apps", primarily with touchscreens in mind
Comes with lots of bloatware like candy crush saga which can't be uninstalled
Notepad, the worst text editor ever made
Paint, the worst image manipulation tool ever made
Updates
Thus forces its users to run an anti-virus software in order to protect them from malicious software
Each anti virus software slows down the system and file system access
Automatically updates the system and disrupts your work by forcing you to restart
A more expensive Windows version is required to be able to disable automatic updates
Occasionally overwrites bootloaders on update, even on other drives
Updates take a very long time to execute compared to other operating systems
Updates can delete your entire home folder
Updates regularly and secretly reset certain settings, like for example the default web browser
Tries to prevent the user of installing and using a different web browser
MS tried to clone apt, but only built an installer-downloader instead of implementing real package management (outdated)
App store
Some Windows versions only let you install software from the app store
Windows will be turned into a subscription model eventually that's tied to its app store
Software dependencies
Lack of proper package management leads to the same libraries being bundled over and over again (outdated)
DotNet bloatware everywhere
Compatibility
Not POSIX compliant
Drive letters
Backslashes as directory separators
Semicolons as path separators
CR+NL line endings
Lots of other incompatibilities with I/O streams, process signals, etc.
Utilities use incompatible and inconcise parameter syntax
No real standard file system hierarchy - every software developer uses their own arbitrary hierarchy
Ignores timezone offsets and tries to set the local time in the BIOS instead of using UTC+offset
Shells and shell scripting
Poor command line shells (Batch and Powershell)
Getting administrator rights requires the user to open a dedicated terminal application
No Unicode/UTF-8 and custom font support in default terminal app
System management
User management unnecessarily complex, putting 99%+ of all systems (single-user-configs) at risk
Administrator rights are no real "root" rights
Poor service/daemon configuration and management
Poor storage device management
Poor and restrictive desktop notifications system
No system-wide inter-process-communication system
Requires booting into "Safe-Mode" in order to perform low-level system management tasks
File systems
Only one proprietary file system (NTFS) supported, which is incredibly slow
NTFS doesn't support checksums, making it unreliable, even in RAID setups
NTFS restricts certain "system-reserved" file names
Can't mount, read from or write to other file systems except FAT
Can't create file names with leading dot in Windows Explorer
Can't create/access file names with a colon in it in Windows Explorer, even though it's supported by NTFS
Network
Internet Explorer and Edge are deeply implemented into the OS itself, which is a huge security flaw
Internet Explorer deliberately ignored web standards for almost two decades
Windows file sharing for local networks set up insecurely by default with access to the user's home directory
No native SSH server+client
Doesn't natively support SFTP (SSHFS), FTPS or any other standard secure network protocols
Graphics
No native DirectX-Linux port (use DXVK)
Forces tripple buffering of the entire desktop environment and its applications run in non-exclusive window mode
Sound
Terrible sound system where each application can choose its playback device individually
Only few sound rulesets
Desktop usage
Only one desktop environment is available (THE Windows desktop)
Uses several GiB of memory in idle state because of bloat- and telemetry spyware
File/program search doesn't work properly and yields irrelevant results in most cases
No real (tiling/stacking) window management
Virtual desktops are very poorly implemented and were only just added in Windows 10
Windows Explorer doesn't have tabs
Windows Explorer doesn't have split views
Windows Explorer creates hidden cache files everywhere for thumbnails and directory stats/configs
Windows Explorer has many redundancies in its menus and also uses a confusing, space wasting ribbon menu
Windows Explorer is tied to the desktop environment itself
Lock-screen requires swipe or keypress for entering the password, but doesn't pass through modifier keys
Themes and customizations
Hideous default theme that distracts the user instead of being easy on the user's eye
Inconsistent styles throughout the entire software catalog of Microsoft
Shipped Windows 10 initially with buggy window decorations and kindergarten-style icons
Custom desktop theming requires proprietary 3rd party applications which replace system libraries
Default wallpaper comes with heavy compression artifacts just to save a few hundred KiB of storage
Wallpapers in the PNG format will always be transcoded into JPEGs with 60% quality, resulting in compression artifacts
Multi-monitor wallpapers start their 0x0 coordinate at the primary screen instead of the most left one
Can't customize the sparsely available desktop keyboard shortcuts
No system-wide icon themes, as icon bitmaps are embedded into executables themselves
File formats
Every .exe file is based on a DOS compatibility workaround
Their "real" office programs use proprietary formats and deliberately ignore (open) industry standards
File/app shortcuts are in a binary format
Internal Windows development
Source code of Windows and all of its components is unmaintainable spaghetti garbage code
Everything has been kept in a mono-repository of hundreds of GiBs
NTFS is close to being abandoned by Microsoft and its developers are afraid to make any further modifications
Envy and realization of their own demise
Windows 10 implements a Unix translation layer and calls it "Linux on Windows"
Microsoft has made lots of efforts trying to switch to Git for the development of Windows
100s of leaked documents and chat logs of (ex-)employees talking/crying about the catastrophic state of MS
Microsoft has released its own Linux distro for embedded devices
There are many rumors that MS will eventually build a Linux distro for the desktop