Hi, I've been doing publishing tool scripting for many years and it looks like your project is fairly complex. I'm looking at your png and it looks like you aren't just trying to script Photoshop, but are also looking at Illustrator and InDesign as well. That being the case I'm wondering if you're doing the checks and validations out of a hot folder or if you're starting on an InDesign file, pulling the list of the linked Photoshop and Illustrator files, then stepping one by one through all the files of the document.
Regardless, it's an interesting project, one I'd be interested in discussing working on.
As mentioned, I've done a number of projects similar (not exactly like it, but similar), the difference being you're just checking files, my scripts usually built something. I specialized in database publishing, but I did have a project that included a number of pre-flight type steps to make sure that a series of checks were made so that when it came time to print everything was right, otherwise a lot of time and money was spent on downtime.
Anyway, if you have any questions of me, please don't hesitate to get in touch.
Thank you,
LaMonte M. Forthun