Why not make a contract/magic item which automatically delivers the food to the correct table, instead of trying to teach kobolds to use software?
If you really wanna help the kobolts learn software, why not create a contract/magic item which helps them do the right thing, instead of having them bother the chef?
That last bit sounds especially like the Ruthless route character. The point of the hotel isn't perfection. It's about humanity. Humanity is full of imperfection. Allowing people to work fairly easy jobs to help travellers who are themselves lost gives them meaning. Automation would only serve to remove that sense of belonging. (And this is veering into real-world issues where I am prone to take the opposite stance, but in this ideal scenario where they are being paid enough to live the rest of their lives comfortably and could also stay without working and still get the same service, I don't the equivalence works.)
It also makes more thematic sense that contract research would result in magical contracts instead of buying and integrating software.
Does it? All of the contract research in the story we directly experience is tied to getting the hotel to understand what a certain technology does. That's why we spend three days with Greta trying to teach the hotel to interpret what the internet is. We see magic throughout, but it's tied to mostly decorations or resources.
If the main character is concerned about security (which he says he is when he considers getting wolfy), why doesnt he make a contract that prohibits violence? It feels like the answer to that question is "Because the hotel doesnt allow the creation of contracts which stray from the purpose...", but it's only assumed to be so, and there should be plenty of workarounds/loopholes/exploits to reach the approximate desired effect. The main character doesnt actually try.
Asterion outright says if you try to sign a contract like that, the ink will just spill off of it. You could have the main character test to make sure Asterion isn't lying, but that goes against the major point of this which is to trust Asterion implicitly since no one up to that point has. There is a way, and that's through mutually assured destruction like the armband that comes at the price, but there's no way Asterion would agree to that when the hotel is supposed to function as a temporary underworld that gives lost souls a safehaven where they can rest before returning on their journey.
This goes back to the first point I was making about automation replacing labor at the hotel, but Asterion is trying to turn this hotel into his version of Asphodel Meadow, since that's the only place he ever felt happy. Asphodel isn't Elysium, but neither is it Tartarus. Like Asterion himself, who should have been in Elysium and had his brother leverage that in order to balance the spite that would have placed him in Tartarus, the hotel is the balance between the Labyrinth's evil and the illegitimacy of his sentence. It's neither paradise, not ruin.