Manual entry seems to have fixed things. Maybe the “#” or the “Persistent Keepalive” were throwing it off? I’ll see if I can find some errors in the logs. Funnily enough, I see a red “Timed out!” error right before it decides to connect, although it’s connected in less than 2 seconds.
What’s also interesting is I had to remove the IPv6 entries (else the manual block wouldn’t validate the entries), but the Azire ones come with them.
Up and running, in either case. But that last bullet point (about the connectivity loss persisting past a reboot on a failed VPN connection) should really be looked at.