Screwed up Debian, any way to fix it

After moving, I fired up the old pogoplug with a working Debian installation on it. I thought it was a good idea to update the system (via apt-get update/upgrade), somewhere along the process, the system froze.
When I try to get access with ssh, I get "connection refused". Without the usb drive, it boots up normally and I can get to the login screen. Unfortunately, I can't remember which password I set up on my.pogoplug.com - and the option to reset it is not there. I am not even sure the pogoplug is correctly connected to that service, by the way.

So, I am wondering if I can re-install Debian on the stick on another computer and just plug it in? Since I didn't change anything on the bootloader, I thought it might be possible?

Thanks in advance

Perhaps a silly suggestion, but when I've gotten connection refused in the past it was because I was just entering

ssh ip-address

instead of:

ssh root@ipaddress

Reading your post again I'm not sure I follow what's going on here. Can you ssh in without the USB attached? Is the login screen you mention the one on the Pogoplug site?

Assuming your ssh command is correct, and the answers to the two questions are "no" and "yes" respectively;you might see what happens if you try to re-register your pogoplug again using the code on the bottom. That should verify whether you are connected properly or not and might give you the opportunity to reset your password. It seems to me that the pogoplug password reset process was a bit obscure and I had to poke around awhile to find it.

BTW I have a pretty good memory but I've started using Lastpass to avoid forgotten passwords online and Lastpass Pocket offline. I keep an encrypted password database locally as my third level of backup which contains all my financial passwords.