I enabled SSH using the first instructions here http://www.jogglerwiki.com/wiki/Ssh the Birds Like Wires Download
I used that to successfully install SqueezePlay, and since then there has been a reboot (or several) of the Joggler. I just tried to SSH in and the connection was refused, before I got to entering username/password. I'm guessing that SSH is no longer enabled - hence the question - Do I need to insert the USB stick at every re-boot to get SSH? (I'd be surprised, but I'm very new to this!)
EDIT: Ignore me - I was using the SqueezePlay manus and got the wrong IP Address - I was trying to SSH in to the receiver not the Joggler

Sorry