Your WLAN IP and your USB IP addresses are different.
Maybe Angry IP Scanner could have helped to find out Jolla's host address.
And as long as your Jolla is allowed to connect to your wlan without entering anything you should've been able to ssh in. Even after a reboot with blank screen your device should autoconnect to your AP and let you in btw. did you ever successfully ssh'd into your device? I'm asking because of the ssh password which is by default generated randomly and only visible in dev mode settings. (in case you didn't set your own password for ssh)
And did you make sure your PC/Mac and your Jolla were in the same net when trying to connect? Operation timed out sounds like your Jolla isn't connected or one of both devices is probably in a different network.

Regards,

J4ZZ