and could you run also /usr/share/doc/obexd-client/examples/send-files 
00:1E:DC:86:44:2D your-file
and see if it output something?.

About the comment #6
> Funnily enough if I click on the bluetooth applet I get a menu that suggests 
> the phone is disconnected (see 
> attached) but I'm still able to get and delete files from the phone without 
> doing anything apart from using 
> Nautilus.

Could you report this to
https://bugzilla.gnome.org/enter_bug.cgi?product=gnome-bluetooth
(upstream bug system)

Thanks

-- 
[Lucid] Bluetooth Send To hangs on connecting 
https://bugs.launchpad.net/bugs/478174
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