The real wins from Docker (for this use case) are:
1. Docker is a better process supervisor than systemd and friends
2. Simple, fast deployment (no manage ansible scripts or rebuild/reboot a machine image)
3. Built-in, standard logging
1. Spend maybe 2-3 full days install kubernetes, helm
2. Spend maybe 3-4 hours installing your app through helm because you're new to installing things in kubernetes.
3. The next app that you want to install on your server is only 20 minutes away, now that you understand how kube and helm work.
Scenario #2:
1. Install app directly on server, hunt down dependencies and other weird things, probably takes 1 day at least, to do the whole installation.
2. The next app that you want to install will take the same amount of time again.
I'd go with Scenario #1 as it is more scalable if I want to install more apps on my server.
I've found using docker-compose is a nice way to do basic orchestration for "self-hosted" type apps.
What distro are you running? Either I am very spoilt with Arch (+AUR) or this is way off the mark.
[1] https://kubernetes.io/docs/setup/independent/create-cluster-...
Initial config surely varies from wall of text config to a simple web based config but popular apps usually have decent doc or googleability to keep you out of maze easily.
Invariably you end up having to add GPG keys for a bunch of weird and wonderful 3rd party package sites, then fight with your package manager to get it to use them, spend hours scouring the web for source code tarballs, spend an age fiddling with compiler flags to get things to build, and... ach! Eventually you're bound to wish you'd never started in the first place!
Also, compiling software is quite normal on Linux. Often it's just `make && sudo make install`, and everything works - but sometimes you've got to go on a goose chase to fulfill dependencies, tinker with compiler flags etc.
It's very normal on Arch Linux at least to pull build files from the Arch User Repository and build the software locally.
The biggest pain point is installation. Most selfhosted software has a ton of dependencies to install first. And after that there's usually some configuration that has to be done before it will work. A complicated installation is enough to drive even tech savy users away.
I've had some luck with my own software by targeting Windows users as well. Most people don't want to setup a linux box just to selfhost a single piece of software.