My wife and I are on her family's business AT&T account as a family plan. I wont go into the boring and complicated reasons as to why that is, but it is relevant to this post. So now that I've gotten that out of the way, also understand this: her family lives in Indiana. We live in Virginia.

Simple right? Well not so much if you want to order new iPhones on pre-order day at 3 a.m. EDT. Why is this complicated? Well, you see, the various carriers make Apple gray out the various text fields during the checkout process of new phones on family plans for the shipping address. And the shipping address is pre-populated with the billing address on file for the account. Supposedly this is "more secure" or some other bullshit. In practice, we just change the billing address on the main AT&T account to that of our home in Virginia for a 5-7 day period, which is just long enough to pre-order the phones and then have them ship to us, and then we change it back to the proper address.

Annoying? Yes. But know that I've worked out the quirks in Apple's ordering system from previous years' experience, which I can only presume they were forced to implement at the carriers' idiotic direction.

Why does all of this matter? Well, this year my wife and I plan to be out of town starting on Sept 25. This, of course, is the day new iPhones will be delivered to people who managed to preorder the devices correctly at 3 a.m. on preorder night. We'll visting friends in New York, but will only be staying with them for two days. I realized this yesterday, which is when I also realized I would need to change the billing address for our AT&T account to their house and then hope that all of the following happened:

I would be able to successfully pre-order a new iPhone for my wife and I without the website or app crashing before the shipping status changed from "arrives on Sept 25" to "arrives in 1-2 weeks" or worse.
If the order managed to go through, it would be delivered without any sort of UPS/FedEX issue on Sept. 25.

What if I wasn't able to order until 10-20 minutes after the website came back up and the order status said ships in 1-2 weeks but my shipping address was already pre-filled in with our friends home address (and thus locked to it)? I would then need to log into AT&T's website to change the billing addrss back to our home address in Virginia - keep in mind I would need to be doing this exactly when AT&T's website has had issues loading in the past from the massive influx of customers all trying to order the new iPhone.

What if something went wrong during shipping and the phones are delivered the day after we leave? This is less likely, but not unheard of.

The more I realized all of the possible things that could go wrong, and are likely to do so, given Apple's unreliable history with pre-orders at 3 am, the more my anxiety levels increased.

I hadn't really came to a decision about what to do when my wife's sister called to ask a few questions about the new iPhone. She wants to upgrade her old iPhone 5S as her two year contract recently ran out. During our conversation, she mentioned the iPhone Upgrade Program so I began explaining to her what I knew about the program, which is basically just the information found on Apple's webpage about it. While explaining this to her, I began to realize the implications of this program...mainly, what's going to happen in September of 2016 with people on this program?

Presumably, I would be already paying a monthly bill to Apple for my iPhone right? According to the plan, customers can "get a new iPhone every year". How will that work exactly? Would that mean that come next September on preorder day, customers who are a part of this program simply select the new phone they want and it is shipped to them when available without having to fight through the entire buying process like we've been having to do for years? This would allow Apple, in advance, to plan for exactly how many of each device to make (with regard to mode/storage/color). Another benefit of this plan is that AppleCare+ is automatically included with the device, which normally sells for $129 as an add-on. And finally, because this is being purchased through Apple completely independent of a carrier "eligibility check", I wont have to deal with any of their bullshit of forcing me to ship my device to the billing address of the account holder.

The Math

Lets look at the iPhone I want as an example:

The iPhone 6S Plus 128GB, unlocked, is $949 off contract. AppleCare+ is an additional $129 for a total of $1078. Granted, you would own this device outright and be able to sell it used to recoup at least half of your cost (based on my previous experience in doing this). But as I see it, any saving you get by being able to sell the used device isn't far off from Apple's yearly cost on this plan.
The same phone purchased through AT&T's "Next 12" plan would be $47.45 per month for a total of $569.40 per year. This is AT&T's plan that would also allow me to get the newest iPhone each year. Note that this doesn't include Apple's AppleCare+ plan or AT&T's additional charge of $6.99 per month for device insurance (as a possible alternative to AppleCare+).
And finally, the same phone purchased through Apple's Upgrade Program would be $44.91 per month for a total of $538.92 per year which includes AppleCare+.

So as I see it, the main benefits of Apple's plan are:

You get a new phone per year, no matter what.
It has AppleCare+ automatically and thus if you screw up (twice per year) and destroy your phone in some manner, you can pay a nominal fee to get a new one.
Upgrading to the newest phone per year could presumably have a much easier process rather than the current gauntlet we have to run each year now being able to ditch any carrier interaction until we're ready to activate our already purchased phone on our carrier of choice.
Finally, not having to worry about selling my used iPhone back online, but instead being able to trade the device back in to Apple for a garaunteed new phone is certainly more conveinent.

The only drawback I see is that according to Apple's website, at 12:01 PDT on September 12, you make a reservation to buy the phone in store, rather than purchasing and having it delivered to your house on September 25. Hopefully my wife and I can schedule this reservation for September 28th or 29th (a Monday or Tuesday of the next week) which would fit our travel schedule. This would also save me the stress of having our phones shipped to an out-of-state friends house and hope it is delivered within the two day window in which we'll be there.

I think we're going to try it. Wish us luck.

Update:

Since I posted this, I've come across two other articles that reinforce my sentiment about Apple's new program.

Jan Dawson, at Techpinons wrote: "The iPhone Upgrade Plan is a Game-changer"

Neil Hughes, at Apple Insider wrote: "If you buy AppleCare+, Apple's New iPhone Upgrade Program Is A Great Deal"