Any would-be switchers, note these are 2 very different things. Self-Hosting sucks, period. For a million reasons that have nothing to do with the OS :) Trying both at once is going to be exponentially more painful than doing either alone.
In my experience, containerization has made self-hosting most software a breeze. The biggest pain points I've come across are related to network architecture and security. I've frequently run into issues with certificates, proxy setups, DNS, etc. It seems like much of that stems around how many modern web concepts were not designed to easily support offline-first environments. Then again, that stuff has never been my area of expertise.
> Self-Hosting sucks, period.
I've been doing it for several decades now, it doesn't suck at all for me.
I think it’s fair to say it depends on what you are hosting and why - personal projects and curiosities, fun! Self hosting business critical data and customer data, minefield! Currently self hosting some little projects, using cloudflare tunnels to serve to the web, and it is surprisingly fun and efficient!
Self-hosting sucks, yes. But I'll be damned if it isn't fun. It's definitely not for everyone. Not only is it not for everyone, but it is not for everyone's families. I'm so grateful that my wife is willing to put up with me experimenting on our home network, trying out different apps, waiting for me to resolve a DNS issue because I forgot to assign a static IP to my pihole.
It is painful but I would say it is also rewarding as I learned a lot doing it!
Hot take alert! As an avid self-hoster, I'd like to hear why.
Personally, I self host because the benefits I receive simply aren't available anywhere else at the level of quality I've come to expect - Jellyfin is a great media player, it's free, and I don't want to switch. Pihole provides ad protection and privacy for my whole home network. It's also free. Homeassistant is amazing, and free. Etc etc.
It depends, do you have the time to maintain few things, or sometimes more than “few things”? Do you have the skills or at least willing to learn? Are you willing to deal with some basic contingency planning in case some stuff goes wrong? What kind of services are you replacing, if emails, probably not worth it, storage? Definitely. Do you have a reliable internet/power combo to rely on accessing your lab remotely? Say you are traveling and want to access your NAS to get a copy of XYZ document, last thing you want is that you are unable to do so because your power is down.
So it really depends on the use case and many factors, if it works for you, great, otherwise and you are willing to pay some subscriptions, then be it.
Half-assing self-hosting sucks, regardless of the underlying platform. You tie things together with shoestrings and gum, leaving ticking timebombs and riddles to your future self.
This is the point where I'm supposed to describe my self-hosting solution on my so-called homelab, where my blog lives. I won't, because it's both stupid in smart ways and smart in stupid ways, therefore it sucks all the way.
Self-hosting is like any hobby. Half-ass it and you'll half-like it.