I'm having problems with openSSH failing to start on reboot on my ipad2, see this thread: OpenSSH problem
I've looked at the log files from a fresh install of OpenSSH and there is a pkg 'serious error' message about the greenp0ison file list not being present in the cydia.log though the pkg.log file lists the package as being present. I wonder if this could be responsible or if it's just a red herring.
Is there any reason that re-jailbreaking would be a bad idea? It might be worth me investigating the Openssh daemon startup files instead.