Isn't this only for people who are new to Verizon?
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I had coffee with a friend this afternoon who went to business school with me

and this is what I think I'm facing. For one thing, I'm not buying a phone tomorrow, though at least I'll be able to make the appointment at the Apple store and also call Verizon and see what the monthly payment is.
Apple Program: $36 and change a month. Can get a new phone every year. If I wait until year 2, the benefit is effectively zero, but then - I assume - I can still take my used two year old phone and get a brand new one. Which makes things simpler. I think.
Verizon: The question for me will be, how much is that monthly payment going to be? That hasn't yet been announced. Regardless, as in the other option, I COULD still switch in a year, but I'd be in charge of selling my phone and paying off the remainder of the 24 month payments. Applecare is my responsibility in this case.
Trade-in for old phone: My in very good condition iPhone 5 will only get about 100 bucks with Verizon, I don't know how much at Apple, and potentially somewhere between 100-200 bucks using swappa, eBay (user has to do the work), Amazon, Gazelle (easier but less money).
So, tomorrow, I make an appointment with Apple, then call Verizon to find out more details. Actually, tomorrow I come here and see what you all have to say, since it'll be faster and likely more accurate. But tomorrow, I think, I will not be buying a phone