Win95 and Win98 still were just GUI applications that ran over MS-DOS. They largely supplanted the MS-DOS underlayment with Windows equivalents, but it was still really a DOS app. WinME tried harder to hide that fact, and that's one of the things that made WinME such a dog.
It wasn't until Win2K (actually NT5) that an MS-DOS-less Windows was made available to the general public. (NT4 was a bit over the top for average users.)
And they still had to provide CMD.EXE because there are some things that a GUI just won't do.
I didnt think nt4 was too hard to use.
On the Microsoft end of things, I started with MS-DOS 5. DOS 6 had a compression feature that I was adventurous enough to use. I was excited to get Windows 3 and at my job at the time they had the Workgroups version of Windows 3 and then Windows 95. I liked Windows NT, Windows XP and Windows 7. It seems to be hard for Microsoft to understand that some of us still use and need desktop computers and we don’t want the operating system to be like something you see on a phone or tablet.