1) You find a way to crash sshd. This might be easier than it seems. Maybe you can fill up a disk partition and cause a fatal logging error, or drive the machine so low on memory that it is killed. If sshd seems too farfetched, pretend you're compromising a less robust system service like the printing subsystem.
2) Try to start your own listener before sshd can be restarted. It's a race, and with enough tries you will eventually win
3) If you're really diabolical, you might notice that there are certain cronjobs or management systems like puppet, chef, ansible, etc that restart system services at known times or after known events (after updating a config file). You write a script to watch for these events (use inotify to event on file updates), and race it to the finish line.
There really isn't a good mechanism from userspace for systemd to police ports without race conditions. Privileged ports is a fairly reasonable way to do it.