It depends. Everything in Hogwarts is handled via Shop Signs where possible, so I used remote shop signs in order to have shops pointing to the chest where the item would be used at. For example, the shop signs for all the Common Room keys point to the chest where the keys go when used to open the Common Room doors. That way the chest will take a very long time to run out of books, and only really as new people continue to go through. Other things have to be done manually, but I have res teleports setup that allow me to do that in less than 10 minutes when I used to do it actively. Plus, if you create enough books, you don't have to reset it that often. Hogwarts employs a lot of what you guys have discussed thus far here, and there were plans to go even further with it. Maybe one day...
I never checked this out and didn't even read the thread, it looks like! Sounds amazing though, I might have to try it some time. Assuming it is still functional?