Are you running this particular unit file as a user unit or a system unit? Some targets like network-online.target don't work from user unit files.

You could also try targeting NetworkManager or networkd's "wait-online" services. Or if that doesn't work, something is telling systemd that you have an IP when you don't. NetworkManager has "ipv4.may-fail" and "ipv6.may-fail" that might be errenously true.

> at that point I might as well go back to init=/etc/rc

The difference is that systemd is much better at ensuring correctness. If you write the invoked shell command properly, it'll communicate failure or success correct and systemd will then communicate that state to the unit. It's still a lot more robust than before.