I see what my problem is:
The checkout script doesn't ask for a password - since anyone is allowed to read my repository this works. It seems that subversion itself is at fault as it just silently does nothing if you try and check-in without it having a username and password cached.

I would say the checkout script needs the ability to specify a username and password, for which probably something more advanced than bash/zenity would be needed. All of this would be very easy in python/gtk.

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