I'm wondering if I am missing out on anything but I can't help feeling that I would struggle to afford a new iPhone every year. Do you sell last year's iPhone to someone else and then use the money to buy the latest iPhone?
My wife and I had been buying a new iPhone every other year until the Apple Upgrade Plan came out and made it even easier to upgrade every year. Before the Apple Upgrade Plan we'd sell our iPhones or give them away to family.
After the Apple Upgrade Plan, you pay a monthly fee for the iPhone ($30/mo for example (when it first came out)) and then after a year, you get the option to get a new phone - Apple takes back your phone and mails you the new phone for about the same monthly rate. (This was obviously in the early days). The 12 Pro Max and 13 Pro Max can be $63-$73 a month now.
Apple makes it INCREDIBLY easy to trade in your old phone. Last iPhone was the first time I got out of the Apple Upgrade Plan and bought on the Apple Credit Card for 24 months 0% interest. Apple offered me something like $790+ for my 12PM when I upgraded to the 13PM. Granted it's a little more than half of what I paid for it but ... makes upgrading frequently a lot cheaper.
Now if I may ask... how do people afford to spend $6/day at Starbucks (not counting waiting in that massive line)?! That's $1600 a year (assuming not going on weekends) and not counting time spent. Hey, if people can afford it, and that's what they want, works for me.
Hope that helps answer the question. Most people I know keep their iPhones for a very long time, trade in for a few hundred.
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Some thinking out loud (and I apologize in advance because I'm horrible at math):
Hypothetical based off of Apple's own resale values: Say you buy a $1600 13 Pro Max. You keep it 3 years. First year's resale is $900, for example. Next year's resale is $650. Third year resale is $350. Let's say the new iPhone in 3 years is $1800.
Keep phone 3 years and sell back to Apple: $1600 spent, $350 back, and buying a $1800 iPhone (in 3 years) = out $3050 over a 3 year period.
Keep phone 2 years and sell back to Apple: $1600 spent, $650 back, and buying a $1700 iPhone (in 2 years) = out $2650 over a 2 year period.
Keep phone 1 year and sell back to Apple: $1600 spent, $900 back, and buying new phone in 1 year at say $1600 = $2300 over a 1 year period or $3000 over a 3 year period.
Doing the Apple Upgrade Plan - $63-$73/mo - you only pay half of the phone's value in a year then get a new phone, so in a sense, you're only paying $800 or so a year vs paying outright like the above - and getting a new phone every year. Apple Upgrade Plan is the way to go if you want to upgrade frequently. $876 year 1, $1752 year 2, $2538 year 3. (For example).
Yes, iPhones are getting REALLY expensive. You really only save $ keeping your iPhone for more than 3 years. I find after 2 years the want and reason to upgrade is fairly strong. I use my iPhone enough that upgrading every year or every few years is a must for me.
Picture of Apple's trade in values at the moment. (May 22 2022).