I upgraded my Win 7 install to Win 10 Home a few weeks ago. Absolutely hated it for 24 hours, then, as I slowly got to grips with the changes, began to fall in love with it. Had a few glitches at first, but now, thanks to some help from the good folk here, it all runs smoothly and I'm loving my "new" pc.
I've been playing around with a full screen start menu and, much as I love it, I have to confess I had the strange feeling that I was covering old ground. I spent a good while putting tiles into groups according to program type, and thought "where have I seen this before?" Then I realised: programs collected into groups, with a nice wallpaper in the background - that'll be Windows 3.11 ! LOL (yup, I'm that old). Still love Win 10 though, and Win 3.11 never had anything like Cortana of course.
In a similar vein, I was clearing out some cupboards today, and came across a folder containing cuttings from old PC magazines I collected some years back as I though they would prove useful in the future. One such cutting was from "PC Advisor" in 1996 and gave a step by step guide to upgrading to Windows '95. It suggested that, when considering the upgrade, you allowed at least 50 MB of free space for the new OS and if necessary, upgrade system RAM to 8MB!! Despite the obvious differences though, most of the advice still held true in principle:- check for drivers; make a backup first; etc, etc.
Bit of a rambling post, there you go, just wanted to share some thoughts.