Selfhosted

The command line is an exceptionally useful tool, you may want to spend a little time getting familiar with it and common command line tools that would probably make self hosting almost anything easier.

It's like wanting to learn to play guitar but not learning how to restring and tune it, sure it's not necessary but you're going to be overly dependent on others to do something you could learn for yourself with a little time and patience, and it will probably broaden your perspective on what you can do once you do get familiar with how to pipe commands together and combine basic tools into something more sophisticated and complex.

Umbrel OS

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

yunohost

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. I don't lile what I hear about Ubuntu) usually for VMs/servers and Windows as the client OS

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

The learning curve might be a little high in some regards, but you may want to try NixOS. There are quite a few services ready to enable and customize for self-hosting, and the design makes updating packages fairly simple.

To be clear, NixOS is not a "simple" solution, but it does work well for self hosting.

Mint or Ubuntu is like Windows but better.

I guess you could install cockpit (via Terminal, sorry, but it's pretty straightforward and there are good guides). After that, you could use the cockpit web interface to deploy docker/podman containers. It's a bit clunky sometimes, but it does the job purely in UI.

You can also manage updates, backups, etc via cockpit if you install the required modules.

As base, I'd use any stable Linux distro that's reccomended for server use.

I'm not trying to be unhelpful. My advice would be to steer into the terminal. Bite the bullet. I use arch and alpine for my servers but Fedora would be fine (but SELinux can be a pain with bund mounts)

Probably just go with Fedora with btrfs for snaps. It has lots of support and is a common choice for servers

• CasaOS
• CosmosOS
• Umbrel

I believe all of these are actually just running Debian as the actual OS underneath, but they give you a webui that makes deploying apps easier.

Of these three, I like the look of Cosmos the most. Seems to be security focused and comes with a reverse proxy and a built in SSO solutions. That’s something that’s usually a pain in the ass to set up yourself.

There’s technically that stupid ass LTT OS but I’m purposely leaving that one out.

If you’re afraid of the terminal, you won’t get far in self hosting. You should learn to use the terminal. It’s not as scary as people make it sound.

You mentioned having issues with SSH into your old server. You can install a desktop environment if it makes things easier for you, but you should still learn how to be proficient in the terminal. Proxmox might help. It lets you create and manage VMs through a web interface. It can be annoying if you’re not super familiar with networking though.