Experimenting with VMs is the way forward.

Basic networking knowledge is vital. And being able to configure your own firewall(s) safely is an important skill. Check out something like Foomuuri, or Firewald. Shorewall is brilliant for documentation and description of issues (with diagrams!) but it does not use the newer Linux kernel nftables and is no longer actively developed.

Go for it with Nextcloud.

I would also recommend at least having a shot at setting up an email server, although I would recommend pushing through to a fully working system. It is possible, and is very satisfying to have in place. The process of setting one up touches so many different parts of internet function and culture that it is worth it even if you don’t end up with a production system. The Workaround.org ISPMail stuff is a good starting point, and includes some helpful background information at every stage, enough so you can begin to understand what’s going on in the background and why certain choices are being made - even if you disagree with the decisions.

Python is great for server admin, although most server config and startup shutdown snippets are written in BASH. You will no doubt have already begun picking that up as you interact with your VMs.

Take the time to properly understand Linux file ownership and permission. Permission will be the cause of many issues you will encounter in you self-hosting journey on Linux. Make sure you know the basics of chmod (change permission) and chown (change ownership), Linux users and groups. This will save you some head-scratching, but don’t worry, you will learn by doing !

Remember that, if you setup everything right, especially with docker, running as root / with sudo is not required for any of the services you may want to run.

Give Nextcloud AIO a shot. I installed bare metal the first time, but AIO has decreased my maintenance burden to next to nothing. Before that, it felt like every update would break my system. I’m a year or two into my transition from Linux nerd to self-hoster. I still fail at things on occasion, but I have learned a lot. I hope it goes as well or even better for you.

the patience to read lots of documentation.

if you could start again in your self hosting journey, what would you do differently? :)

That’s an excellent question.

If I were to start over, the first thing that I would do is start by learning the basics of networking and set up a VPN! IMO exposing services to the public internet should be considered more of an advanced level task. When you don’t know what you don’t know, it’s risky and frankly unnecessary.

The lowest barrier to entry for a personal VPN, by far, is Tailscale. Automatic internal DNS and clients for nearly any device makes finding services on a dedicated machine really, really, easy. Look into putting a tailscale client right into the compose file so you automatically get an internal DNS records for a service rather than a whole machine.

From there, play around with more ownership (work) with regard to what can touch your network. Switch from Tailscale’s “trusted” login to hosting your own Headscale instance. Add a PiHole or AdGuard exit node and set up your own internal DNS records.

Maybe even scrap the magic (someone else’s logic that may or may not be doing things you need) and go for a plain-Jane Wireguard setup.

You don’t need to be a programmer to selfhost.

The most important “skills” to have if you want to selfhost imo are:

• Basic Networking knowledge

• Basic Linux knowledge

• Basic docker/docker compose knowledge

But I’d say to not get lost in the papers and just jump right in. Imo, the best way to learn how to selfhost is to just… Do it. Most everything is free and fairly well documented

• Docker: You can practice on your main computer before complicating things with networking.
• How to set up a reverse proxy: DNS, certificates, etc. I recommend Caddy.
• Backups: If you use Docker Volumes, make sure you back those up too and test the backups.

To self-host, you do not need to know how to code.

One thing I would do differently is setup LDAP and OIDC so you can use the same authentication credentials for different apps (at least the ones that support them). I use LLDAP and Authelia for this purpose.

I think if you have a mini PC or something you don’t mins installing server specific OS on, proxmox VE is pretty great. It can be a bit of a headache depending on what you want to do but it also makes expanding your self hosting super easy/fun.

Proxmox let’s you created virtual machines or containers and easily manage them.

Currently I run a mini PC.(Beelinks are great for this and pretty cheap with more power than a raspberry pi)

1. Proxmox VE as the operating system
2. Jellyfin as my media server

• looking to install home assistant and some others as well.

3. Tail scale to use as a VPN into my network privately from anywhere.

Simplest set up? No. But I also just started self hosting. You’re gonna hit some.headaches regardless but it’s also extremely rewarding and I’ve learned alot.

Edit: if you’re only wanting to run one thing (say jellyfin) . A raspberry pi with tail scale and jellyfin is how I started. Works just fine.

Docker really. If something goes bad, trash the container and start again without loosing your actual data.

Learn how to properly backup your data in case you nuke something you shouldn’t

If you want to program something, the closest you’re gonna get to programming is Ansible and Bash scripts.

You might want to get self hosting hardware like Synology or the like if you’re not ready to dig.

Otherwise here’s some things you need to know:

• Docker
  • Easy, consistent deployment of services in their own environments. Think a VM but with almost no overhead.
• Docker Compose
  • Run docker containers with consistent configuration in files.
  • Connect various containers to each other on the same or different networks.
  • Get multiple containers to start together and talk to each other.
• Systemd
  • Manage any service on Linux. If anything needs to start on boot, restart when crashed, start on timer, you want Systemd.
  • You can manage your docker compose containers lifecycle via Systemd.
• NGINX/Apache/Caddy
  • A web server for reverse proxy. You’d probably need one at some point, especially if you want HTTPS. Your services get hidden behind it.
• ZFS
  • Reliable redundant storage. You’ll need storage. Use ZFS with 2-disk redundancy.
  • Supports automatic snapshots for recovering from oopsies. E.g. deleted something or some software shat on your data.
  • Can use recertified disks from serverpartsdeals.
  • Can use USB disks or USB box with multiple disks. If you end up going the USB route, ask me for tested hardware.
• Backup system
  • Something to do backup. There are many options.
• Ansible
  • If you want to write code that describes your services and make them happen, you want Ansible. You write code (well YAML) and Ansible installs things, writes config files, sets up Systemd services, restarts things. It can be convenient especially if you have a lot of stuff and you want to be able to see all of your infrastructure in code in one place and be able to version it.
• Prometheus
  • Monitoring your stuff. Is my backup service running? If not send me an email.

Oh and use Debian or Ubuntu LTS.

I don’t know how to code, but I did a lot of internet searching on the commands to use (since I was also new to Linux). When I started to self host I was lucky the projects I wanted were popular enough that they had good documentation. Eventually after spinning up a lot of services I got the hang of the general structure of docker compose files and that’s the extent of any kind of new language I learned, haha

Persistence and reading comprehension.

There’s no need to learn Python or any programming language to self host stuff, you just need to be able to follow blog posts and run some Docker commands.

I’m a software dev and haven’t touched a single line of code on my NAS. Everything is docker compose and other config files.

You don’t really need to know a specific language to self-host anything. But things like YAML, JSON, Docker, and some networking basic will go a long way.

If I could do anything different though, it would definitely be to write more documentation. Document the steps taking setting things up, log notes on when you have to fix something, archive webpages and videos that you used along the way. Currently doing that myself now after some time self-hosting.