Both of these Windows annoyances can easily be solved.
Never delete anything ever again. Turn off your computer and go out into the fresh air and sunshine, skip happily through fields of daisies and buttercups ... no, hang on.
The file deletion user interface mechanism in Windows 9x is pretty ridiculous. Most people put up with the tedium of going through all the motions. (Labour saving hint : don't empty the Recycle Bin straight away each time! Let it grow and grow for a bit. Think of all the effort you're saving not moving the cursor all the way to the leftmost edge of the screen.)
Those who use the "Smart" deletion method of pressing shift invariably get burnt sooner or later. But the most annoying (and evil) thing of all? If you have a non-FAT partition sharing the same disk as your Windows boot partition, irrespective of whether you tell Windows to ignore it or not, after emptying the Recycle Bin it will "helpfully" offer to format that drive!
"Are you sure you want to delete? Yep... Are you sure you want to delete (it's a program file)? Yep... Are you sure you want to empty the bin? Yep... Are you really sure? Yep, Yep, Yep... Are you sure you want to vape your work OS? Ye... no, wait!"