Unless something has drastically changed since I switched to Linux around 10 years ago, Windows did not at all have a "universal package". Instead, installing software meant manually downloading an installer from the vendor's website and then manually interacting with that installer through a GUI. Windows installers come in a variety of different (even custom written) formats which essentially make it impossible to automate package management in a universal way.
Back then Windows had already blessed Windows Installer packages (.msi), which could be installed unattended from the CLI. But, to be fair, many companies still preferred to use other installer tools, including sometimes Microsoft themselves (e.g. ClickOnce).
But there's been improvements. The winget CLI can now install and update several well-known applications, and even upgrade them when you first downloaded them any other way. There's also the MSIX package format, which is much closer to distro packages or mobile apps, can auto-update without a central repository and supports sandboxing.
Nowadays, even if still a bit hacky, I definitely consider Windows packaging less painful than the mess that is Linux distribution. Packages in distro repositories are regularly outdated, and every other package is installed misconfigured or has been patched in unclear ways by the distro maintainers; then there's Flatpak which make for gigantic installs with clunky sandboxing, or AppImages.
Use Debian Testing. This is the _rolling_ release from the Debian family.
And don't be fooled by the name of the release: "Testing". The name "Testing" exists due to an orthodox approach of Debian community that only the Debian stable can use "stable".
This is only true until testing gets frozen. After a freeze gets lifted again, many transitions might occur. I use it myself but it's wrong to call it a rolling release that everyone should use.
testing is absolutely not a rolling release. Sure it gets new packages faster than stable which can appear to be the same as a rolling release it gets frozen before a stable release and suddenly it's not a rolling release.
So to describe it precisly: Debian Testing is a rolling release for majority of time. When the Stable is going to be released, Testing gets frozen for a while. But then it becomes the rolling release again.
Debian stable gets released once in ~2 years. So once in ~2 years Debian testing is not a rolling release.
