I've worked at a couple small companies that strongly prefer self-hosting services that aren't core to their business. I'm at one now, in fact (though it's not nearly as bad as the first one). My conclusion from these experiences is that it's almost always a bad idea. It's a waste of money if you have people dedicated to managing them, and if you distribute the tasks to people who'd otherwise be working on your product(s)—even if their contributions to that would also look like sysadmin/ops work or whatever—then you're engaging in pointless distraction.

Some managers/owners seemingly don't mind spending $4,000+/m in payroll to chase $2,000/m savings in paid services, though, for whatever reason.

I say, just pay the $$-$$$/month for each thing, and be done with it. If paying for the service isn't worth it, paying someone to manage the tool internally almost certainly isn't, either, so prefer attempting to do without it over that option.

[EDIT] obviously, this can change with scale. If you're a huge company then putting an average of 1/4 of the hours for five sysadmins to managing a self-hosted chat tool can absolutely save you lots of money over paying for one—provided the reliability's at least as good. A small slip on that and you're back on the wrong side of things.

Interesting, I've always worked at places that prefer to pay someone else for the trouble and use a ton of third-party tools for all the things.

In the end, do you think the self-hosting route is worth all the trouble and costs?

It's certainly cheaper to have a couple of sysadmins, but then again, it depends on how valuable is the stuff you're dealing with. Small web agency? Probably not. Supporting dozens of journalists (like my org)? Absolutely.

There are also trade-offs. A few sysadmins can't host emails against hostile (sometimes state-sponsored) parties like Google can. We can't roll out a better messaging service than Signal. We could roll out our own VPN, but if the goal is getting lost in the noise, you want a popular VPN, not routing journalists' traffic through unique IPs.

On the other hand, just Nextcloud and GitLab (two fairly common services) require about 10h/month if you don't want to be major versions behind or miss security patches in minor versions.

Would you mind to elaborate on the VPN thing? We do work with journalists as well and we see private Wire Guard configuration as a better option, as nobody knows that’s a VPN a journalist connects to.