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.

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.

Generally, Linux Servers are best administered from a command line. At least in the beginning to set everything up. In turn they are faster on lower hardware as they dont even have a graphical desktop at all so need less resources. You could of course install a windows server OS. They can be fully administered through Remote Desktop and a GUI.

There are multiple projects to make self hosting more accessible (like casaOS). They automate many steps of the setup and then offer you a webUI for further steps. Maybe have a look here https://github.com/awesome-selfhosted/awesome-selfhosted?tab=readme-ov-file#self-hosting-solutions

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

Unraid is great for beginners.

Almost all of selfhosting is editing config files, setting permissions and starting/stopping services.

Setting it up so you can administer a server by desktop is probably as hard as learning how to edit config files from a terminal. Maybe harder.

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 as I don't like what I hear about Ubuntu) primarily for VMs and servers and Windows as the client OS

Keep in mind the reason why people generally dont run desktop environments on a server is because unessential software uses more resources and increases the chance of a system crash. I would highly reccomend learning how to use a terminal and installing fish (shell) is a great place to start.

For what it's worth given the age of this thread and disagreement going on in it, I would recommend Unraid.

Easy for a beginner, with enough to take you up to intermediate level: a web GUI for pretty much all the required terminal commands. It's been around for years, is not going away, but instead getting updated. Works on any old eBay hardware and most of all, the community there are very supportive of beginners. There's also lots of YouTube tutorials.

It ticks all the boxes for easy self hosting. It's just not for Linux protocol purists.

EDIT: I'm learning a lot from this thread, and it's interesting to see how tolerant people are for self hosting. I would add in my vote for Unraid: it allows me to be dynamic with the time I have for self hosting. I'm sometimes extremely busy and don't have the time to keep my self hosting updated, so the web GUI is essential for basic maintenance. Then there are times when I do want to waste an afternoon trying something in terminal and learning more, and that's when Unraid again comes to the rescue. I couldn't self host with 100% terminal, and neither would I want to with 100% GUI. The best self hosting platform is one that can mix them up efficiently and effectively. I am keen to try some others mentioned here, as some look quite interesting. However NAS is a massive element of what I need for my homelab, so Unraid will stay for now.

I can recommend you Debian, since it's the "default" for many servers and has a lot of documentation and an extremely big userbase.

For web interfaces, I can recommend you, as you already mentioned, CasaOS and Cockpit.

I used CasaOS in the beginning and liked it, but nowadays, I mostly use Cockpit, where I have the feeling that it integrates the host system more, and allows me to do most of my maintenance (updating, etc.) quite easily.

CasaOS is more aesthetic imo, and allows you to install docker containers graphically, which is better for beginners.
I personally do my docker stuff mostly via CLI (docker compose file) nowadays, because I find it more straightforward, but the configuration CasaOS offers is easier to understand and has nice defaults

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.

• 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.