Apple don’t know that you have OCD unless you tell them, and even if you had done so when confirming with them that it was OK to order two iPads, the staff member you spoke to was probably talking generally and did not note it on your account or cancel any restriction that might have been placed to prevent the orders from being shipped.
Apple can probably legally refuse to ship you an iPad, on the basis that repeated cancelling of orders costs them money, looks dodgy (they don’t want the police to take the view that they haven’t done enough to detect and prevent crime) or at the very least, is a nuisance. They aren’t refusing your custom simply because you have OCD, which would be illegal in many countries.
It may be that Apple/the small claims court end up considering whether or not your pattern of ordering is something that a person with OCD would reasonably do. How many Pro orders did you cancel before deciding you wanted two other iPads instead? If they were all the same configuration, reordering wasn’t going to magically get it to arrive sooner, unless you ordered for collection at a store that had it in stock. Changing the configuration would have been a more reasonable thing to do if you were set on getting the iPad quickly, given that stock levels of each will vary.
I have come across cases on consumer forums of people having credit stuck with Wayfair and Amazon because they would no longer allow the customer concerned to place an order.
