I think I can make this work, I've planned it out a little but I'd still like to hear your rant.
I'd probably group them by what kind of food they like and give them all a few sentences going into the details.
Something like...
MEAT
Groudon - Steaks, so well done they're almost burned to a crisp.
Heatran - Steaks, always wants a bigger one than Groudon.
SWEETS
Mewtwo - Likes anything with artificial flavors or sweetener
Shaymin - Pancakes with lots of syrup or honey from her own flowers
I probably wouldn't make a new image for each Mon since the AI struggles with putting food and characters together sometimes, but each grouping would have an image of the food, like some BBQ for the MEAT section