The way I understand it, You would need the $100 plan. You will need to provide a copy of your receipt. The plan will only pay you for what you spent, minus taxes. It does not pay for what the item should have cost originally. You might what to double check with their customer service. they have been very helpful to us and my two claims were paid very quickly back to my PayPal account.
According to a customer service rep for Square Trade, their warranty bought on Amazon would cover only products bought on Amazon as well. Your option is to buy it directly from Square Trade, either by calling or using their website. At least for tablets, a full copy of a sample service agreement is provided on their website.