If you're at all well-versed in Vegas, poke me on skype, I have some questions and whatnot.
Largely the video above explains the primary issue I'm having right now but overall, theres probably some other smaller ones I could bring up so... yeah.
Edit: The more I look back on it, the more I realize it appears to be a resolution issue...
Is that something I can fix in Vegas or do I need to take every single image back into PS to fix it?
[ sci·am·ach ]
/sīˈamək/
A simple, angry man casually working his way through life on a personal quest to acquire copious amounts of street cred.
Both the background and foreground images have to be set in the same aspect ratio.
Go to each image's Video Event FX > Preset and select an aspect ratio.
After this is done, you should be able to scale the foreground image and move it anywhere on the screen. The background image may be cropped, but I think this should work.