Even then, there’s a warning that the upgrade process can take several hours. Even if it’s largely hands off, that’s not exactly my image of an easy upgrade.

Specifically upgrading major versions. See the official documentation for upgrading Debian 11 to 12. It’s far more involved than minor version upgrades.

https://www.debian.org/releases/bookworm/amd64/release-notes/ch-upgrading.html

Here’s the official documentation for upgrading from Debian 11 to 12. The TL;DR is that it takes 8 chapters to describe the process.

https://www.debian.org/releases/bookworm/amd64/release-notes/ch-upgrading.html

The problem is when it comes time for a major version upgrade. Debian 12.10.0 to 12.11.0 probably won’t be a big deal. But upgrading from Debian 11 to 12 was a pain. Debian 12 to 13 will probably be a pain as well.

The thing with Debian is that yes, it’s the most stable distro family, but stable != “just works”, especially when talking about a PC and not a server (as a PC is more likely to need additional hardware drivers). Furthermore, when the time comes that you DO want to upgrade Debian to a newer version, it’s one of the more painful distros to do so.

I think fedora is a good compromise there. It’s unstable compared to RHEL, but it’s generally well-vetted and won’t cause a serious headache once every few years like Debian.

The thing with Debian distros (like Ubuntu, Mint, PopOS) is that they’re extremely stable releases. This does not necessarily mean everything “just works”, but rather that they will not experience major code changes that could disrupt a working system. This means that if some apps don’t work out of the box, that state is going to be pretty much the same in any distro based on the same Debian version.

A more “agile” distro might be less stable, but as a result could see some updates to apps that Debian is still lagging behind on. Fedora is probably the “next step” in this direction: it’s still reliable but gets updates more frequently than Debian (it’s sort of a “proving ground” for code before it gets pulled into Red Hat, which is a distro focused on long-term stability).

As for desktop environments: I’ve always thought GNOME was the most Mac-like DE, but KDE has enough configuration options that you can kind of turn it into anything you want. Since this is on a very old laptop, you might consider LXDE, which isn’t the prettiest DE, but it’s super lightweight and might let you squeeze out a bit more performance if you’re wasting a lot of compute power just rendering the desktop.

$100M of $VT, secure my ultra-comfortable retirement right then and there.