This pricing is confusing, and it seems the apple upgrade program is significantly more expensive than a 2yr contract. For example, the cheapest apple upgrade program is $32.41/mo. That's $388.92 after 12 months. Afterwards, you have to give the phone back. Previously, with a 2yr contract, you paid $199 up front. After two years, you can even trade it in for credit, say $100. So after 2 years, you paid $99 ($199-$100).
The argument can be, fine, you're not locked into a contract. Ok, i can see that. So using the logic above, by avoiding the contract and choosing Apple's upgrade program, you end up paying $289.92 ($388.92-$99) extra to avoid an additional 12 months contract.
In other words, by doing the apple upgrade program, your paying $24.16/mo ($289.92 / 12) for the ability to upgrade every year versus every two years, and you get apple care included.
Am I missing something? IMO, not worth it.