For what it's worth, I tried to something similar using Thinstall.

I had to stop working on it because it was taking a lot of time to figure out, but am may take it up again soon for another project (in wxperl) if pp and an open source installer don't hack it. My problem in the past was that I couldn't get pp to install or run without crashing on the pc in question, and I really wanted to do it all in cygwin.

Thinstall is nice commercial software and ought to work for Perl too, basically it makes a virtual filesystem you can pack all your files into. I was trying to pack apache, postgresql, and perl with its core modules into one archive to run a cgi using Class::DBI and view it in a browser.

Needless to say the archive was heading around 40 mb last I saw it..

Since you don't need a database or apache your case is more interesting. If you can figure out the dependent modules using pp, theoretically you could run it out of a thinstall archive (which would look like an exe). On the other hand you could also just use pp to package the main program and install the other files using an open source installer, which is a little less clean-looking but on the other hand, is a lot cheaper.

Would like to see how you solve the problem. I looked around for virtual filesystems in an exe (or something from unix that could be applied) and the thinstall unix tools demo, which gives you a shell with many tools all in one exe, had stuck in my mind. My advice is first check out par's pp. Good luck!

Matt R.