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Dependencies in the IT Shop

I've been looking at the IT Shop and wondering if some functionality is available to do with dependencies. The following logic is what I want to implement.

If user requests item x and they don't have item y, automatically request item y as well.

If user requests item x and they already have item y, request only item x.

 

I've looked at how service item dependencies can work and the three options that are available but none of the three seem to fulfil these two requirements. The closest option is to set 'It is compulsory to request this service item at the same time'. This works for requirement 1 but not 2. In the second case this will not allow the order to be processed since item x is already requested and not multi-requestable.