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I never expected this forum to question/push back against yearly upgrading! This is one rational group of fanboys! lol
Lol I think the year-over-year changes have just gotten so small for iPhones that it's far less enticing than years previously. I love everything about my 15 Pro Max and will not upgrade until next year. If I had any year previous, I would upgrade this year because of USB-C. The fact I have one connector to charge my iPhone, iPad, MBA, and MBP is so convenient. Not to mention the laptops in our clinic/hospital are USB-C Dell computers so if I forget my charger at home, can charge any of my devices.
 
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Instead of wasting money on new iPhones every year that are virtually identical, isn’t there anything else you’d want to play with instead?
How about a new bicycle?
A new e-bike?
A new electric scooter?
Anything except an iPhone?
OR what about spending it & investing in one's retirement funds/stocks/bonds/mutual funds? Our future selves could have so much more money/security if we could only control our spending today. And yes, these yearly updates are so small that it's wasteful financially and environmentally (i.e. having different cases, chargers, accessories that only fit the current model - the e-waste just adds up with every upgrade)
 
OR how about we not tell or suggest to others how they should handle and spend their money...
Well, it was open to discussion per the OP:

"Does buying outright and selling on eBay or Swappa make the most sense, or go with the iPhone Upgrade Program, or some other approach?"

"Or some other approach" they said.
 
Im on tmobile and they have 2 year phone "contracts" where you trade in a certain phone and get $800 or $1000 off (certain phones get eligible for $1000). So I buy the cheapest phone on that list that gets the $800 or $1000 and trade that in for a new iPhone. Im usually on a two year cycle, so when the new iPhone comes out my current one is ending its "2 year tmobile contract" and I am free to sell that phone usually on facebook marketplace.

I did this last year with the 15 Pro Max launch. $1200 for the 15 Pro Max + a $100 device to trade in = $1300. Got the $800 promo applied so it was $1300-800= $500. Sold my 2 year old 13 Pro Max for $700.

Effectively made $200 upgrading. Have to be on one of the most expensive plans on tmobile tho :/ Works for our family (about 5 phones getting upgraded every 2 years)
I have T-Mobile with the go25g. I should get decent trade on my 15 pm
 
I have T-Mobile so I use their upgrade feature on my plan. I basically turn the phone in and get new customer pricing so it ends up being a free upgrade for me.

As a result, I will be snagging the iPhone 16 Pro.

I do my upgrades via Apple directly though.
Although when you use T mobile ,instead of say Mint, you are over paying at least $ 30-50 per month.
 
OR how about we not tell or suggest to others how they should handle and spend their money...
This is an open forum and not a group chat between friends. So both you and whoever else thinks OP's ideas are irrational or the thing to do can say what they what.

My own odd take is that I'm "starving" myself to bring back the flavor and excitement to upgrading.

Like, how are you going to get excited about ice cream and hamburgers if you have it every day? When the chef only barely tweaks the "menu"? Just because you can afford it?

Sounds very, very boring to me. A kind of boring I'm not spending $999-$1199 at every single year. No way.

My next iPhone has to make me excited or I won't upgrade. I'm hoping it's this year's. But I'm not counting on it or letting the hype push me.
 
I used to upgrade every year by buying the iPhone in cash and selling the pervious one. But there is not much changes between generations of iPhones anymore. I only upgrade once every few years. This year, it’s because I really want USB-C because everything I own charges that way, and Apple Intelligence. So two big things that I am wanting. Paying $1000 every year for just ONE new thing is just a waste of money in my opinion.

I have 4 kids (college/high school age) so it actually works out really well for me. My wife and I will now upgrade every year and 2 kids get "new" phones that are only a year old, next year rinse and repeat, other 2 kids get 'new' phones. Those of us that use of phones to make a living have best battery life and technology, kids are within a 3 year cycle, everyone wins.
 
iPhone Upgrade Program. Easy, no hassle for me so far.
Same. First two years were painful because they required you to be physically at the Apple Store to pick up/trade in phones. Now that they'll send it to my doorstop all is well.
 
I just trade in every year. I think I got $500-ish for my 14 Pro? Really takes the sting out of updating.

I'm with Google Fi, so no upgrade program for me.
 
I upgrade through tmobile’s JUMP program. Pay off 50% of the device (so 12 monthly payments) and turn the old phone in in order to upgrade after the first year of a two year contract. I pay taxes on the new phone and, in previous years, $0 on the phone itself… but this has been a rough year and I have a shaky payment history, so they want a $370 deposit this time—which I’ve saved for. Still better than trying to come up with $1200 outright.
 
I’m trying to get more scheduled/organized about regular yearly iPhone upgrades and am eager to hear some best practices from the forum on how to optimize it and how to minimize the expense.

Every third year I have been taking advantage of AT&T’s $1000 off after eligible trade in and that works well for me but am now trying to assess my approach in the other two years. Does buying outright and selling on eBay or Swappa make the most sense, or go with the iPhone Upgrade Program, or some other approach?
Upgrading every year requires one to be ok with losing money to get the upgrade. A lot of the people on the forum take part in the Apple upgrade program, which is nothing more than renting, unless one decides to buy the phone to complain the loan rental agreement.
 
When the iPhone 15 Pro came out, Apple had an amazing carrier deal going on for T-Mobile that basically meant I got to upgrade for free by trading in my 14 Pro and paying like $100 for the taxes. Hopefully, this year it’s the same.
 
OR what about spending it & investing in one's retirement funds/stocks/bonds/mutual funds? Our future selves could have so much more money/security if we could only control our spending today. And yes, these yearly updates are so small that it's wasteful financially and environmentally (i.e. having different cases, chargers, accessories that only fit the current model - the e-waste just adds up with every upgrade)
What if you unexpectedly die shortly after upgrading? All that you mentioned above is now irrelevant, but if you upgrade you get to spend an extra couple of days with your 16 pro max
 
This is an open forum and not a group chat between friends. So both you and whoever else thinks OP's ideas are irrational or the thing to do can say what they what.

My own odd take is that I'm "starving" myself to bring back the flavor and excitement to upgrading.

Like, how are you going to get excited about ice cream and hamburgers if you have it every day? When the chef only barely tweaks the "menu"? Just because you can afford it?

Sounds very, very boring to me. A kind of boring I'm not spending $999-$1199 at every single year. No way.

My next iPhone has to make me excited or I won't upgrade. I'm hoping it's this year's. But I'm not counting on it or letting the hype push me.
Sure boring. So what? One spends $x per year (not $1200/year, but $1200 less the value of last year's phone) which translates to $1 to $2 per day for the value add of whatever boring features the latest iPhone may provide to any particular user. In my case using the iPhone camera for work, most years the new camera competence is hella worth half the cost of a cup of black coffee.
 
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Yearly upgrader here… pay outright and trade in the old one to . I used to sell online, but like others, the hassle, fees, risk of getting scammed wasn’t worth it to me anymore.
Is there a standard trade in value for the base Pro each year? Eg is it always $570 trade in value on launch day for the prior years model? Or does the trade in value change year over year?
 
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I get a new iPhone every year since the first iPhone was released in 2007.

For the past few years, I’ve been trading in the old iPhone and pay the remaining balance with the cash back I’ve accumulated throughout the year using the Apple Card. Some years I have a very small amount out pocket, and some years I net to zero.

Before Apple Card and before trade ins, I used to buy the new iPhone upfront out of pocket.
 
Historically I've had the iPhone 3GS, 5, 7 and now my current 12.
I'll be getting the new 16 Pro and trading in my 12 if they accept it.

I've got the cash ready to buy the new 16 but I might keep that in the bank and buy it on Apples interest free plan paying monthly over 2yrs.

By the time I fancy another new iPhone my current 16 will be paid off and I'll just rinse and repeat.
 
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When the iPhone 15 Pro came out, Apple had an amazing carrier deal going on for T-Mobile that basically meant I got to upgrade for free by trading in my 14 Pro and paying like $100 for the taxes. Hopefully, this year it’s the same.
How much is the monthly charge and how long ?
 
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