Selfhosted

Hey OP, I'm just starting my self-hosting journey as well. I can program a little bit in Python and C++ but I haven't needed any of that so far. As others have said, some familiarity with Linux would be very helpful. The things I've done so far:

• Wireguard VPN server on my router(no programming or linux commands, just some config of my router which I was able to do in the router's GUI.
• Wireguard VPN client on some of my devices. My phone setup was easy, still working on setting that up on my Windows/Ubuntu laptop.
• Home Assistant on a Raspberry Pi (WIP).

Eventually I plan to set up a NAS with Immich and some local IP cameras and Plex or something similar.

It depends on what you want to self host.

As an example, a family member self hosted home assistant. They didn't have to know anything really. That was all they were doing and they bought the canned implementation.

If you have multiple services, you may need to know nginx configuration with virtual hosting.

You may want to use podman or docker or kubernetes.

It all depends ..

Along with the things others have said (Backups, Linux, Docker, Networking) I'd also recommend getting comfortable with server and network security. A lot of this is wrapped up in the simple mantra "install your goddamn updates!" But, there is more to it than that. For example, if you go with Nextcloud, read through their hardening guide and seriously consider implementing all of the recommendation. Also think through how you intend to manage both the server and instance. If this is all local, then it is easier as you can keep SSH access to the server firewalled off from the internet. If you host part of your stuff "in the cloud", you'll want to start looking at limiting down access and using keys to login (which is good practice for all situations). Also, never use default credentials. You may also want to familiarize yourself with the logs provided by the applications and maybe setup some monitoring around them. I personally run Nextcloud and I feed all my logs into Splunk (you can run a free instance in a docker container). I have a number of dashboards I look at every morning to keep an eye on things. E.g. Failed/successful logins, traffic sources, URI requests, file access, etc. If your server is attached to the internet it will be under attack constantly. Fail2Ban on my wireguard container banned 112 IP addresses over the last 24 hours, for 3 failed attempts to login via SSH. Less commonly, attackers try to log in to my Nextcloud instance. And my WordPress site is under constant attack. If you choose to run Wordpress, be very careful about the plugins you choose to install, and then keep them up to date. Wordpress itself is reasonably secure, the plugins are a shit-show and worse when they aren't kept up to date.

Patience, most of all.

Also, backups and notes. The solution you use to host might take care of the backups. For example, I use Unraid, so if any drive fails the system can simulate the data on that drive until I can get it shut down to replace it, and then recreate the data on the new drive.

As for notes, those are important so that you can always know what you’ve done, and what you need to do. That way, if you ever have to do it again, say if you’re setting up another server or replacing one that failed, you know the steps you took to get it set up exactly how you like. It’s also handy because you’ll be doing things like assigning services to ports, and you’ll probably at some point want to know what services are on what ports without going through and checking each one. Things like that are handy things to stick in notes.

Other than that, you don’t need a lot of skills to set something like a home server up. You just need to read the documentation for each service you’re planning to use, and get familiar with how it works.

Why are you wanting to use python for self hosting? Python is a programming and scripting language.

There are two big things I would focus on. The first thing is networking, the OSI model and http basics. The other thing I would look into is Linux containers. If you can get both of these you are golden. Learn how to use and write docker compose files and then looking into building your own containers with Dockerfiles. You don't really need to build your own containers but it is good for learning

Programming knowledge is largely irrelevant, as in to gain sensible benefits from it you have to be generalist software engineer with decade+ of experience of seeing it all. Then yeah, you can read any code, any stack traces and figure out the intent of developers of the system and what is undocumented/incorrectly documented.

Focusing on one particular language is the right and wrong answer at the same time. Wrong in a sense that you'll have to pick up other languages along your journey anyway and right because you need to achieve mastery in one of them to get to more advanced programming topics. Pick a language that you have fun using and don't care about anything else.

As for what to learn for self-hosting... Linux (pick a distro, let's say ubuntu LTS w/o gui, ssh there and get comfortable with it. It includes installation, filesystems, RAID setups), networking, HTTP/S (that's the main thing you'll be interacting with as self-hoster and knowing various nuances of reverse proxying is a must), firewalling, basics of security and hardening, docker, monitoring, backups.

attentiveness

If you have a VM, there is no need for docker. Start by installing ssh. Enable public key auth. Disable password authentication. Set up fail2ban with ssh. Set up ufw. Set up nextcloud. Avoid hosting your own mail, that's another level of complexity. If you really need it, try mailcow.

If you have all that and didn't touch a GUI on your way, you're good to go.