1) A waste, they should have put the effort into NT (first released in 1993). It set back the PC industry by nearly 5 years, destroyed NT Security (people writing 32bit programs and ignoring security settings because only NT used them), it killed the Pentium Pro (no easy return to 16 mode)
2) Autorun was the stupidest thing ever.
3) The Entry level spec wasn't enough memory to have TCP/IP, Word and Browser at same time.
4) The first version had no USB.
5) It was really just WFWG 3.11 with Win32s, VFW, and 32bit disk driver all bundled with a new better shell, but file explorer was inferior to File manager has STILL has some of the same bugs/stupidity, like you have to hold shift or control to be sure to Move or Copy, if you lose track of which drives which folders belong. Still Explorer file copy is primitive compared to xcopy. Why are overwrite options broken and can't be set at start? Why no copy only newer etc. Only NT3.5 was a real 32bit Windows.
6) Office 95 deliberately used specially invent APIs to stop it running on WFWG. Which made it fail on true 32bit NT 3.5, so they brought out NT3.51 with later tech preview of Exporer Shell.
7) They added the worst bits of Win95 (and later Win98) to NT4 .0 (and later Win2K and XP)
8) The "Start" button should have been called Main, Main Menu or Menu. Start is stupid, as in many cases it was only used most days to "shut down".
9) Ran 16 bit code natively instead of on a VM like NT. (NTVDM and NT WOW)
10) Could only connect to named Pipes. Couldn't create Named pipes. The stupidest 32bit / NT feature to omit. Forces use of COM and shared memory evils instead.
Later "Personalised Menus" and desktop clean up and hiding icons in Task Tray was UTTER stupidity as then how do you find the less used things or even know they existed.
GUI only went down hill after the initial improvement of using the desktop better than previous "Program Groups". The nadir being ribbon and then making buttons/menus look like ordinary text. Stupid on windows, web and Kobo. Where the hell you supposed to click/touch?