FWIW I've been using Ubuntu desktop with CasaOS for a couple of months now to host Nextcloud, Jellfin, Immich and a few other bits and bobs with absolutely no issues at all so far!

I honestly would use a headless Linux system with docker compose. You can find premade docker compose files.

I misread that as "self-loathing" and the answer was obvious.

(I’m not very good with the command line)

Me either so I take a lot of notes about commands and command sequences. Also, I find that Grok is pretty decent at explaining commands. AI is a wonderful tool, but you also need to do your due diligence in ascertaining whether AI has given you the correct information. I would not copy/paste random commands into a production server, but rather I have a small test server for that kind of stuff. Once I have the command, tested, and understand the command, I can then use that in a production environment.

In as much as I love a good WUI, you will have to learn some cli, it's just inevitable, especially in a headless environment. It may seem daunting at first because there are literally thousands of commands and command sequences. I honestly doubt if even the geekiest nerds on the planet know all by heart. For each command sequence, there are probably hundreds of ways to compose the same command. I would admonish you to download Notepad ++ and start keeping notes on the commands you use. Later on, the fun part is looking back on your notes to see all the commands you now know and what they do.

Core utilities (like ls, cd, cat, etc.) from projects like GNU Coreutils provide around 100-200 commands. Additional tools from packages (e.g., grep, awk, sed) and system utilities (e.g., systemctl, iptables) can add hundreds more. On a system with many packages installed, running compgen -c | sort -u | wc -l in a Bash shell might show 2,000–10,000+ unique commands, depending on the setup.

I personally use Debian. For your case, you can install lightweight desktop environments such as XFCE.

Honestly from my point of view after reading your post, you don't have a terminal or operating system issue, it feels like you are new to self-hosting and don't know how to start configuring from scratch.

Ideally you want to look for documentations or keep asking for online help. For example, with installing docker, you would want to refer to this: https://docs.docker.com/engine/install/. Welcome to system admin life, where you spend more time reading/understanding than configuring.

Personally, you can even use AI Chatbot to help you with stuff, just be specific on the system you are on, the goal you are trying to achieve and the problem you are tring to solve.

Which brings me to answer your next point about CasaOS: It exists so that you can skip most of the 'system admin life' step. It skips almost all the setup you would have needed to do on a fresh machine, and just leaves configurations. The downside is usually it eats up more resources than a self-configured install since it comes with redundant features you are unlikely to use.

TLDR; Pre-configured OS such as CasaOS is a solid choice if you just want to set it up and be done with it. If you are here to really learn about system admin stuff, then pick any of the Linux Operating system (Debian-derivatives recommended) with a lightweight DE.

Happy self hosting :v

i tried CasaOS for a quick minute. its decent and just has the basics like setting up any disks and then has an app store. its really just a front end for docker and you can manually input the details of any docker containers that arent in the store

ive mostly been running docker stuff on my Synology nas. cant think of the model number now, 218+ i think, but any of the "plus" models will let you run docker. its very similar to Casa, no messing around with command line stuff. ive been self hosting for 10 years now and never touched the command line so i dont know what people are on about here saying you will have trouble

dietpi is another thing ive used on a few devices, mainly small SBCs and raspberry pi's, but i think they might have a version that you can install on anything. its basically just debian, and it has a sort of a wizard that helps set up various things like set up disks and install apps. its headless though so no GUI unless you install one, and the wizard is run from the terminal but youre not having to type any commands at least

I am very much a Windows user and my journey went like this:
Raspberry Pi with OMV -> SSH on OMV -> Mostly Terminal on OMV -> Docker + Portainer to deploy containers -> Transition to docker-compose -> Setup my own VM with Debian completely in the CLI (excluding the first setup of the VM)

I use Linux (primarily Debian because of Raspberry as I don't like what I hear about Ubuntu) primarily for VMs and servers and Windows as the client OS