I don't like installing packages outside of the apt/aptitude system. Creating a custom .deb requires a repo to store our fork of the code (or the code + our configuration parameters) plus a jenkins or similar job to build it, plus a place to store the build artifacts to make available to our fleet of boxes, which also need to be configured to pull images from said repository. There are many potential points of failure now. Rarely do I have package failures with my current infrastructure.

I'd rather trust the package/security team of my favorite distribution to do this for me.

When you live in the modern world of cattle not pets you optimize for things like this.

That being said our current nginx solution lives in a Docker container on top of Kubernetes so it would be fairly trivial at this stage to build our own nginx and bake it in... but I have to pick my battles.

I found that nginx actually "just works", however not all software is easy to compile and many of us shy away from compiling for various reasons.

Compiling nginx is surprisingly easy and straightforward; a perfect example to get started with packaging for yourself.

Indeed - but having built an nginx module, it's hard to convince others to use it. Often, nginx users are simply using the binary packages from their Linux distribution, and if they compile their own, they'll have to remember that they have a version that's compiled from source on the system and not the packaged one.

Exactly and then when it is time to patch nginx you can't just install a new binary and reload - you have to have documented exactly right set of modules previously compiled. Depending on the modules this can be time consuming and error prone. Not impossible, but adds additional automation requirements.

Time of compilation is one issue. If you just wanted to add a module you would have to recompile everything. Likewise if you want to remove a module.

Although one advantage of requiring compilation is the user is probably more likely to use the latest version.

you can reduce re-compilation time by using ccache compiler caching. i do this for my Centmin Mod LEMP stack auto installer and re-compile via ccache is up to 60-80% faster than without ccache https://ccache.samba.org/ :)