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I'm a little disappointed that they seem to be very uninterested on how to get it working on "unsupported" configurationsI think that's entirely reasonable. Unsupported configurations are "unsupported" for a reason: because open source developers have a limited amount of their unpaid free time to devote to their project, a project you get to use for free.
> ... was closed by the developer as "only two people have asked about Gentoo"
Again, entirely reasonable. Maintaining installation scripts for your project for every OS under the sun is a large burden, especially for OSes that the developers don't personally run themselves.
Since Linux distros are basically the poster-child of fragmentation, the usual way to get a piece of software supported on your distro is to have a distro package (for Gentoo I guess that'd be an ebuild) that does any distro-specific patching. Stuff that's generic enough can be upstreamed. Stuff that is distro-specific often has to stay in the distro patches unless someone is willing to step forward and be trusted to actively maintain it upstream in the long term. As an open source project maintainer, I definitely would not want distro-specific code in my build if there's no one with the inclination or expertise to maintain it.
> essentially saying "please install package X/Y/Z" during setup
... and this is exactly something that goes in your Gentoo ebuild, not in PiHole's generic install.
> I know Gentoo is fairly niche as far as distributions go, but seeing popular software moving away from "here's how to compile/install it" to "here's a docker container/here's what "we" support" is very disheartening
I'm a little puzzled by this remark, since that's how it's always been with open source that's intended to run on Linux. I go back and forth on what I think about Docker, but before we had that, you basically got a tarball with a configure script, and had to figure out on your own what dependencies to install on your distro to get it to build properly. Some projects with more bandwidth would include an RPM Or DEB package, but oftentimes those would only run on a few specific versions of RedHat/Fedora or Debian/Ubuntu, and you'd still have to install the dependencies yourself. At least with Docker it's sorta a "build once, run anywhere" type thing.
The thing I don't think you're getting is that you are not entitled to these people's time or resources. They're putting out a project in the hopes that people will find it useful. It is not reasonable to expect them to cater to every whim of every potential user's personal setup.
I'm sorry for the long-winded reply here, but it really bothers me when people expect open source developers to have their free time directed by non-contributors.