Frankly I am extremely tempted to move over to the Apple Upgrade Program. It significantly simplifies the process of owning the latest and greatest. Boom, just easy monthly payments and a trade every 12 months. I definitely get the enjoyment out of upgrading each year that would make it worthwhile. Simply, I love the program. Never having to think about the upgrade process again at a reasonable cost is a major plus.
But... through my experience purchasing an iPhone yearly I have found a way to do so cheaply. Stay with me for a second as I explain: I purchase a new iPhone, take the SIM card out, and place a tablet on the line to make an otherwise $40/month line cost only $10/month (then use the iPhone on my main line, removing my previous iPhone at no cost). Verizon allows customers to do this, and reps even have recommended it. With the new changes, to my surprise Verizon still allows this for customers on the older plans.
Thus, the cost of purchasing an iPhone on a contract then transferring the contracted line to a $10/month tablet line is quite a bit less than the upgrade program.
Let's do some math:
Buy 64GB iPhone 6s Plus for $430 (with tax) + $40 activation fee + switch line to $257 ($24 * $10.70) tablet plan = $727, net $500 after fees selling phone = $227 cost per year
If we want to compare apples-to-apples we can factor in the cost of AppleCare+ although I don't personally purchase it. Since the AppleCare+ cost is $129 for two years of coverage let's say that's $65/year so the cost is really $292 if we perfectly compare it.
Apple Upgrade Program: simply purchase for $42.45/month * 12 = $509 cost per year.
Frankly I have a way to save an additional $150 on buying a new iPhone yearly through promos by creating a new line so the cost disparity is even higher.
Now, if Verizon closed the tablet contract loophole then the Upgrade Program would be a no-brainer but I am giving up my ability to upgrade cheaply each year to upgrade more conveniently. Although, another plus of the Upgrade Program is that it would allow me to forgo my upgrade date of December 2016 on my main line for the iPhone 7 (Plus) but I could simply begin the program next year.
Hopefully my math helps those out there on Verizon on older plans deciding whether to use the Upgrade Program, and this thread can help me decide

. I'm paying a lot more for convenience but if I do it another way I probably won't have my 6s Plus until October/November.