I can't confirm the first time issue, I just tried with a guest session:
- start guest session
- click on nautilus in the launcher
- do alt-printscreen

-> the screenshot dialogs open with a screenshot of nautilus

Changing the keybinding to alt-printscreen doesn't work indeed

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https://bugs.launchpad.net/bugs/1244253

Title:
  Alt+print is non-functional, at least for 1st. use in a session &
  cannot be reset in an ubuntu session

Status in “gnome-control-center” package in Ubuntu:
  Incomplete

Bug description:
  Test case:
  open a window, go alt+print (PrtScr
  What happens:
  either no screenshot of window or one may get a fullscreen shot & or Hud may 
open
  Expected result:
  a screenshot of window

  Disabling the Alt binding for Hud makes no difference

  To note - this now only seems to happen on ist use of Alt+print in a
  session though Hud always opens

  Test case:
  Open system settings > keyboard > shortcuts > screenshots > click on "Take 
screenshot of window",  press backspace to disable
  Then click on again to set new accelerator > try to set alt+print (prtsrc
  What happens:
  Nothing

  Expected result:
  would set to alt+print

  ProblemType: Bug
  DistroRelease: Ubuntu 13.10
  Package: gnome-control-center 1:3.6.3-0ubuntu45
  ProcVersionSignature: Ubuntu 3.11.0-12.19-generic 3.11.3
  Uname: Linux 3.11.0-12-generic x86_64
  ApportVersion: 2.12.5-0ubuntu2
  Architecture: amd64
  Date: Thu Oct 24 10:18:49 2013
  InstallationDate: Installed on 2013-10-03 (21 days ago)
  InstallationMedia: Ubuntu 13.10 "Saucy Salamander" - Beta amd64 (20131002)
  MarkForUpload: True
  SourcePackage: gnome-control-center
  UpgradeStatus: No upgrade log present (probably fresh install)
  usr_lib_gnome-control-center:
   activity-log-manager          0.9.7-0ubuntu4
   deja-dup                      27.3.1-0ubuntu1
   gnome-control-center-datetime 13.10.0+13.10.20131016.2-0ubuntu1
   gnome-control-center-signon   0.1.7~+13.10.20130724.1-0ubuntu1
   gnome-control-center-unity    1.3+13.10.20131004-0ubuntu1

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