Is what I mean is having a way of setting bundles of different items in the same chest, like say 32 sugar cane, 32 carrots, 32 potatoes, 32 melon seeds, 32 pumpkin seeds and a diamond hoe in one group and when that shop sign is activated, all of the items in the set group in set quantities are sold.. Or maybe even a sell all function that sells all items in a chest that can be used so that the bundles can be made manually in different chests.. This is an just a little idea to make it possible for bulk buying of multiple items to be streamlined and not as time consuming.
Not a bad idea, though it sounds hard to implement. Maybe you could just do a regular shop sign, but have "all" on the last line, or maybe [slot1-7] to sell the items in slot 1-7. The tricky part is letting the buyer know what they're getting. That may be possible by using the upcoming spectator mode, though. +1 for a neat but not urgent idea. In the mean time, there are ways to sell bundles using redstone, but they're kind of tricky and require faith on the buyer's part. I think salesman200 has one on one of his res's, but I haven't tried it.
I think it won't be too hard to let them know what they are getting. Just have a confirmation and ask the users to click on something in the chat to confirm. If we want to get fancier and keep the chat less crouded, a dynamic thing that when hovered over will show the items. For example: You are about to buy multiple items for *rupee amount* Click here to see what you are buying Click here to confirm