I think Debian Server + Docker compose. Its the easiest way to get started and has the most documentation for. To me, the OS itself is the least concern - just get something maintainable. Then choose services you want from https://selfh.st/apps/ and have a go with them. Most services give you docker compose scripts so that is by far the easiest way.

If there are two of you with accounts, then I would suggest these:

• Reverse proxy (caddy, nginx, etc)
• SSO authentication (authentik, authelia etc)
• VPN for access (wireguard, netbird, tailscale etc)
• Security (fail2ban, crowdsec, etc)

On top of Home assistant and the Jellyfin / arr stack you mention, I would recommend Immich (google photos), Paperless NGX (letter scanning / management), Vaultwarden (password manager), FMD (find my device server for android phones), and SearNGX (private search engine).

Potential alternatives would be NixOS (fully scripted) and Proxmox (better containerisation but still got to decide what you install on each container, such as Debian + docker). You could also use podman instead of docker compose, which is more secure but a bit more effort to adapt to. However, if access is only through the VPN and you have two users, Debian + docker would be fine.

Adding to this - first thing I self hosted was vaultwarden so keeping track of the admin accounts is so easy. Make an admin account at the start to set it up, then only use that in a private window for any settings changes needed. My personal account is then like a normal user which helps me test it and keep it separate. I try and use SSO for everything so it also tests if that works correctly - I.e. after setting it up I’ll login to my personal account on the SSO to see if it registers correctly and that my username is given regular access.

Vaultwarden - self hosted bitwarden server that any bitwarden clients can connect to.

What difficulties are you finding with it and are you switching from Google? The results are as custom as Google given they haven’t scraped your life history so wondering if that’s it? I’ve been using DDG without any issues. About once every 6 months I struggle to find something so try the Google bang but have never found better results. In fact, I was shocked last time how crap the Google results were, just full of AI generated crap and SEO based crap.

To be honest, DDG is also struggling with that now as it’s based on Bing. I have been trying a public searxg but not found it very good so far.