So my first Windows 10 upgrade from System 7 went so smoothly on my tower, that I updated our laptop last night. Also really smooth. I like the fact that they put a tool bar on the second screen. For things that one is forced to do, or else, this was a pretty good experience.
That's great, happy to hear it.
I was not so fortunate, when I upgraded my Win7 Pro a couple years ago. Luckily it was a VM (virtual machine) so I just made a copy and tried the upgrade on that. Seemed okay at first, but then the first time it did Win10 Upgrades it went unstable. So I ended up getting a Win10 installer ISO file, and did a fresh installation of Win10 from scratch. That has been fine ever since, including upgrades, although I skipped 1809 which was generally viewed as a disaster. After 1903 came out earlier this year I did another fresh install using the same product keycode, copied my applications over, and it's fine.
Since you're doing okay so far, my only advice is, do regular backups. If your installation is "on the metal" (not a VM), I personally like Acronis True Image, but there are good competitors too. If it's a VM, just make a copy from time to time in case things go sideways.