Don't apologize, this is great info. We did find a problem on our end and we've corrected it. I just did a test for a very large PDF (112 pages) and it worked, BUT it took quite some time. That's a lot of pages to create.
When you output with the catalog, there is a busy thingy that runs telling you it is working on it so you don't think it is broken. We've haven't gotten that set up for the Fashioner yet. You get no feedback, so you just have to sit there for a bit. On my test, it took less than 2 minutes (felt like an hour). Please give it another try and let me know.
No idea what the issue is with the ad image button. I'll put that on the list to fix. 😃