If something "spreads to the hildon side" then you know it isn't a problem with your Debian chroot. That sounds like a problem with environment settings; I get that problem when using "sudo" to run commands that use D-Bus.

As for the "out of space" problem, the only solution is... get more space!

I guess I should include the e2fsprogs package, so you can resize the image file with resize2fs... but as soon as you start doing that kind of stuff, you're out of "Easy Debian" territory. You might as well set up a partition with enough space.