I started in the mid-90s, and though I didn’t use 95 much I did use 98SE (which is aesthetically very similar to 95) and 2000 plenty.
For releases with the classic Windows look, I think 2000 is best. It makes a few refinements to the theme that at least to me make it more pleasant to use than 95/98.
I started well before Win95. I can still see that Aero was MS's peak UI, even though I never seriously used the OS myself (my workplaces all seemed to skip Vista).
For releases with the classic Windows look, I think 2000 is best. It makes a few refinements to the theme that at least to me make it more pleasant to use than 95/98.