When doing the resize2fs.. I prefer to just copy the debian resize2fs to the maemo /usr/bin.

That eliminates the need for a PC with Linux, or Chrooting into Debian and resizing a second image file. This way you can just resize the original.

Highly recommend backing up the original of course - in case things go bad.. but if you are tight on space.. there's no reason you can't use the debian resize2fs from within maemo if you copy it over.