Just some initial more thoughts on this topic:
Sometimes I think what happens is (Especially with Apple), you have someone who has been a loyal follower from a specific company they appreciate they purchased their products over the course of years, where they spent thousands and thousands of dollars in products for their household, workplace, personal use case, etc. And once they’re ‘let down’ that one time by the company, because the company refused to make an exception to their documented policy which clearly lists the provisions, The consumer feels they should be entitled to something after all the business/money spent they have given them over the years. But the reality is, there is a policy in place that clearly states XYZ and that loyal customer is nowhere even near being inside the policy guidelines.
Now, the question is posed, should that company make an exception just because this one ‘loyal purchaser’ who spent a large amount of money on their products be treated differently based on the status how much money they spent? Or should that company treat all their customers equally in the sense that if someone is well outside the return policy, nowhere does it state that Apple should have to make an exception to anyone for anything.
In my opinion, the OP emailing Tim Cook is a desperation move, and it’s not necessary to be emailing/bothering the CEO of a company because of a decision they made to purchase a product that they’re well outside the return period. I understand purchase mistakes happen, however the OP already knows what to do for reselling the iPad, but they refuse to do it, because they think that some other ‘special course of action’ should be given to them as a privilege they should not be allowed to have. Again, I hope Apple does not make an exception for something this person does not deserve, not when this is their own mistake.