What is the correct action for systemd to take here? After a timeout it will do what you said it will do, but until then it will try to do what the configs have said it should do.
You can tweak this however you want. You can shorten the timeout to whatever you want, you can change the dependency graph so that particular unit does not depend on the network, you can disable it completely.
> It's this "punch the user in the face" style of user interface design that I object to that is so prevalent in the corner cases of modern UIs.
I don't understand what you mean here, it was configured to do one thing, and it did that thing. You can of course say that it's a bad config (which is probably true), but then it's either the distro, the packager, systemd's defaults (which often are not ideal) or your own customizations. I'm all for arguing about better defaults in systemd and making distros better config their packages, but the actual systemd init seems to have done exactly what it was told to do here. Again, I'd like to say that distros/packages/users of systemd treat it like a pure init and often don't use it as intended.
> I can't run systemd-analyze when the system off in lala-land for 5+ minutes.
If the tree of critical services for your boot are that broken I'd assume you need to boot into single user mode or use a recovery usb. But if you actually boot after those 5min I'd expect you to easily find where those 5mins where lost using the tools I mentioned above, which is more than I can say for previous inits.
Those who do not try to understand history are doomed to repeat it. That has clearly happened in the case of systemd and is why I don't think the attitude it presents towards end users is at the level that such a core piece of infrastructure should display.
Maybe your distro supports LDAP or another remote user directory? Maybe you just have some services installed that depend on the network and that say they are critical to the multi-user.target? You haven't given enough info for me to know, but it probably isn't systemd's fault in this case.
Because one of your other services has said it depends on network.target/network-online.target and is in the critical path of your boot. Check which one with "systemd-analyze plot > plot.svg" and "systemd-analyze dot 'network.*' | dot -Tsvg >network.svg". You can also see the critical chain and which parts block faster boot with "systemd-analyze critical-chain".
I think if you stopped expecting systemd to act like something else and instead treated it like the toolkit that it is you'd see that it does what it says it does quite well. Those issues with boot you mentioned are often that the distro ships a bad systemd config for a certain program.