I'd personally be interested in specifics if you're willing to provide them.
I put this together a long time ago, and some of it may no longer be valid, and the rest will be picked apart for inaccuracy, but for what it's worth:
Modern Operating SystemsIf the hard drive requires reformatting, some registered programs must be re-registered.
More effort has gone into hiding data and information than has gone into making it easy to work with.
Tired of the response, "Well what else is there?" when talking to the average Joe about alternative platforms and operating systems.
Modern software designers have never heard of buttons called Use and Test, and have no concept of what the word Cancel actually means.
The desktop is at the highest position in the device hierarchy, yet it's really a subdirectory on the boot drive. The hierarchy should have the drives at the top and work its way inward, not take some arbitrary starting point and pretend it's the top.
Modern OS users seem oblivious of the difference between Screens and Windows. Here's a hint: if the entity being referred to can be moved or resized, then it isn't a Screen (unless it can only be dragged upward and downward, and then it's not Windows.
Ever intend to drag the contents of a window which may be positioned close to the window's edge, and instead get the pointer too close to the border, drag it and inadvertently resize the window? Wouldn't be so bad if you could cancel it before letting go of the mouse button.
Most, if not all Windows-only users who know what wildcards are think that *.* and ? are perfectly adequate wildcards.
Microsoft tells us where we are to save all of our data. What ever would we do without them helping us with such difficult decisions? Heaven forbid we try to save our stuff in a place that differs from the norm.
Modern operating systems are programmed to be task-oriented rather than user-oriented, giving more importance to what the computer wants to do and less to what the user wants to do. Operating systems of the past had the opposite feeling. Regardless of how "slow" the hardware, if the system became unresponsive it was usually because of something which had gone wrong rather than simply being standard operation.
If the application is busy, accessing menus is impossible.
Let's put the close gadget right next to the "minimize/maximize" gadgets. Who cares if the user clicks the wrong one and loses all their work. We'll just have extra "are you sure" requesters to ensure the user feels both protected and annoyed.
Why are the scroll bar arrows separated by the scroll bar? Isn't the idea of scroll arrows to keep from having to move the mouse while scrolling?
When the system is busy, the entire GUI appears frozen. Often there is no indication that this is normal. The system simply fails to respond.
Progress bars that use 10 - 20 pixel wide segments have been widely adopted by many applications in modern operating systems, foregoing a more comfortable and informative pixel-wide segment.
How can a computer crash so hard that it no longer accepts input from the keyboard?
There's usually no clean way to cancel an errant mouse click. If the user intends to drag-and-drop something, clicks and starts to drag it, then realizes before dropping that it shouldn't be dropped, most operating systems won't let the user cancel it easily without the risk of dropping it in a potentially dangerous place.
Buy it, use it, throw it away.
Modern operating systems don't support two-image icons.
Just try renaming a "folder" or a file while it's being accessed in any capacity by any other application.
Students in today's "I.T." studies are being taught to underwrite software, leave behind bugs and use poor implementation methods in the name of job security. Students I've spoken to will attest to this new ideology.
Windows don't conform to a user-defined default position and instead either recall the last used size and position or default to what the programmers feel is appropriate for all users. How about allowing the user to tell the operating system when to save window position coordinates rather than saving them every time the thing is moved?
Scroll gadgets snap to their original position if the mouse is moved an abstract distance from them.
PCs are 70s technology. The Y2K problem is clear evidence that the original designers of the PC never imagined that it would still be used beyond the 20th Century.
Complete incompatibility with other platforms. Initially Microsoft will announce and release a new format and open the source to developers. Then after it's been widely adopted, Microsoft changes the format and withholds
the sources.
If DOS is really gone from Windows, why can't I put backslashes and colons in file names?
More often than not, the Microsoft Wizard is less helpful than just allowing the user to configure something manually. Getting Windows to realize this and allow manual configuration can be more difficult than actually getting the thing configured.
The Start Menu actually reads source files linked by shortcuts before the user clicks on anything. Normally not a big deal, but when the source file is located on a network or a drive that spins down, the whole start menu freezes while the drive spins up or the network connection is made. It can be quite lengthy if the connection times out.
It's become common practice not to include any form of documentation within installation packages. In many cases, the only way to figure out what software is or does is to install it. Then, if it isn't what's wanted or expected, uninstall it, which usually leaves bits of the program behind.
Any clicks on a specific letter of text existing in a text gadget is ignored in favor of Windows' desire to highlight the entire line, requiring a second click to put the cursor where the user originally intended on the first click.
Instead of naming system files something useful, they're given cryptic 8.3 file names in combinations of numbers and letters even though the OS has supported long file names for over a decade.