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I tend to gift mine away so not bothered about cost retention. The phone is paid for and written off once the contract ends.
If your buying a 1 year old phone by the time you own it it's a 3 year old model. No wonder you give them away would be worth 1/4 of new price or less.
My scenario doesn't work for you. Your way you are paying near full price for a 1 year old phone for another 2 years, doesn't make sense to me, then rinse and repeat, talk about being behind the 8 ball.
 
If your buying a 1 year old phone by the time you own it it's a 3 year old model. No wonder you give them away would be worth 1/4 of new price or less.
My scenario doesn't work for you. Your way you are paying near full price for a 1 year old phone for another 2 years, doesn't make sense to me, then rinse and repeat, talk about being behind the 8 ball.

Don’t worry yourself over it.
 
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My wife and I have been buying new phones every 2 years through our provider on contract. The last contract we signed was 30 months. We have been very content with our Iphones after 2 years and would like to not upgrade for another year or two, but each time for the last two cycles one of our phones bit the dust and we had to trade up. Gonna try real hard to get 4 years on our current Iphone 13's.
 
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Every single year. I have a problem. Also, it doesn't hurt that I generally get around 85% of my money back when I sell the previous model, which goes toward the new model. I don't use the Apple trade-in, because they pay peanuts.
 
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2-3 years previously, but I plan to keep my 13 pro until it loses support.

I buy my phones outright from apple and hand down my older phones, so trade-in/sale value is irrelevant.
 
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We are on a 4-6 year cycle normally. Usually the adults in the house upgrade while their older phones get passed down to the kids. Then the oldest phone get turned in for credit toward the new phone.

Although we tried to have a battery replacement done on my son’s 12 this week and that turns into a fiasco of scheduling, miscommunication, and changing details every time we tried to work it out. So guess that one will be traded in this fall when new deals come out.
 
I used to "Upgrade" every year but now i honestly cannot justify the price or find enough of an upgrade to warrant the latest iPhone!

The only reason i jumped from my 12 Pro Max to the 14 Pro Max was the fact my battery life was so poor on my 12 Pro Max that i just decided to ditch it!

Im hoping to keep my 14 Pro Max until maybe 17 Pro Max releases.
 
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