Many nice programs have been stated here but I'd like to throw Media CMS in the mix

Write the post and then upload the image?

The other way around. They've invested in so much real estate they need to justify it.

I use trillium that gets backed up every hour to my pc.

I also do a lot of python development so my project ideas get written down there too.

I'm not a fan of code is documentation because what happens when you step away for a month and you need to figure something out? In trillium I have a search bar. What do you have in the code?

I’d rather not mount the docker sock into my reverse proxy,

You don't have to if you use the dynamic file config. I've mentioned this before and debated to the ends of earth for even suggesting such a thing. But it all aspects is dynamic file configuration better.

Of you use IaC in your set up, it gets even easier because then you can just set up templates that automatically create file configs and add them to your reverse proxy seamlessly.

Right now with one Terraform apply, I create my docker container, traefik config and my homepage service.

Headscale the self-hosted server is unofficially but decently supported by tailscale the company. They employ the dev and don’t seem to be trying to kill the project or mess with it much.

Probably because they're smart and realise the people who self host probably wouldn't spend money on tailscale, and those who'd buy tailscale subscriptions wouldn't have the time/resources to self host it. Win win.

I suspect they are both using the same interface wg0. I did a quick Google and it looks like you can do the following in gluetun

WIREGUARD_INTERFACE=wg1

This is my suspicion as you're using essentially two wireguard instances at the same time.

Trilium for notes, Jellyfin, jupyterlab and komga

Sorry. The question have a harsher vibe than I expected it to

https://hub.docker.com/r/banhcanh/docker-fmd2

Not the prettiest, but supports the most websites. Can even add your own sites if you don't see it them listed.

Why don't you just get fmd2? You can just have it download the webtoons for you when new ones come out.

You have to give sonarr access to your top level media folder. Then you set sonarr up to hardlink the downloaded files to your media folder.

E.g. if you have home/media/tvshows and home/media/movies, give sonarr access to home/media. Your download client should probably have a folder like home/media/downloads in your sonarr app map the downloads folder to a sonarr folder in the downloaded client settings. Then set all imports to hardlink, instead of copy.

Your Plex/Jellyfin server should point to home/media for your library where the hardlinking occurs.

I would go a step further and use ansible to manage the devices. Set it up to auto update and you'll have basically no maintenance.