Sorry What I gave was a little rudimentry...

The issue becomes more apparent when more files are being selected

I'll attach a screenshot so that it becomes more clear.

Try to recreate the following scenario found in the attachment
screenshot.

If in windows (or any other desktop environment / OS) I would select
logos -> case oakland university, then ctrl+select case_ubuntu
locatrix_v1.pdf, then ctrl+select fables_01_aesop.spx, then
ctrl+shift+select oo-about-these-files.odt (this would select everything
in between), then ctrl+select oo-derivatives.doc, then ctrl+shift+select
oo-presenting-ubuntu.odp.

currently in nautilus, it doesn't work this way, as once you have
selected file(s), you cannot reselect many files using shift without
losing your current selection, or if you use ctrl+shift which most users
would attempt to do, you may only select one file at a time.

I hope this makes it easier to understand... I'm not very sure on the
terminology / a better way to explain, and am trying to do the best I
can. Please DO point out better ways to explain it / any questions you
have.

** Attachment added: "gnome nautilus multiple file selection"
   http://launchpadlibrarian.net/16376404/Screenshot.png

-- 
ctrl doesn't work when used in conjunction with shift click for multiple file 
selection
https://bugs.launchpad.net/bugs/252817
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