Can you publish the Keyboard Maestro macro?
What oddities in Ms Word did you see?
Depending on how the images should be arranged, I can imagine a Word macro that is called by Keyboard Maestro.
There are many VBA macros dealing with images.
Examples here, here, here, or here.
For calling a Word macro from Keyboard Maestro, use this simple AppleScript:
tell application "Microsoft Word"
run VB macro macro name "test"
end tell