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Not Lua:
In my opinion the best way to deploy software on windows is with an installer.
I would suggest to take a look at NSIS ( http://nsis.sourceforge.net/Main_Page ).
With NSIS you could pack everything nicely into one file, install everything silently and even generate (installable) patch diffs with vpatch
( http://nsis.sourceforge.net/VPatch_plug-in )
The "downside" is that you still have the to deploy the whole directory (but create nice desktop links to start your application).

David Krause