On creating an exe, check out Perl executables? or perl to exe - they go through a couple of methods you can use.

For the printing, I would check out Win32::CtrlGUI, for instance:

use Win32::CtrlGUI;

# Open file - do other stuff

my $window = Win32::CtrlGUI::wait_for_window(qr/$filename/);
$window->send_keys("^p{2}{ENTER}!fx");
[download]

You'll have to play around with it - I have no idea if this is right or if it works... but I hope it sets you on the right track.

Best,
  -Adam

Update: I played around with this a little - and actually think this is quite a cool set of utilities... Now this isn't perfect, but I have some working code for you - it opens a file, sends command-p to print, hits enter in the new window - then exits the app, by hitting alt-f, then 'x' - again, not perfect, but quite enjoyed playing around with this mod...

use Win32::CtrlGUI;

$file = 'Untitled-1.pdf';

system("start $file");

my $window = Win32::CtrlGUI::wait_for_window(qr/$file/);

$window->send_keys("^p");

my $window2 = Win32::CtrlGUI::wait_for_window(qr/Print/);
$window2->send_keys("{ENTER}");

$window->send_keys("!f{1}x");
[download]

Update 2: Also, if you have any trouble finding Win32::Setupsup, as I did, just (ActiveState): ppm install http://theoryx5.uwinnipeg.ca/ppms/Win32-Setupsup.ppd