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Every year, I pay the whole cost upfront for the biggest, fanciest iPhone unlocked directly from Apple. This year, I will be selling my iPhone 11 Pro Max (256 GB) on eBay and buying the same size 12 Pro Max. I should get about $900-$950 for it as it is in mint condition. Accounting for eBay fees, PayPal fees, and the taxes I'll pay on the new 256 GB Pro Max, it will essentially cost less than $500 for me to upgrade.

Older iPhones obviously lose value each time a newer model is released, so I am paying only a tiny bit more than if I upgraded every 2 years or every 3 years and did the same thing. I would start saving serious money only if I kept my current phone for at least 4 years, and as a tech enthusiast I just can't bring myself to do that -- especially considering that this is a device I use for multiple hours every day.

In other words, upgrading your iPhone every year is actually not stupid or particularly expensive assuming you pay upfront, keep it in good condition, and sell the old one on eBay. Using this method, I am paying only a fraction of what those on Apple's yearly upgrade program pay. I understand that not everyone is in the financial position to do this, but if you are and are a tech enthusiast like me, I think this is the best way to do it. :)
OP I agree whole heartedly. People often ask “why do you upgrade EVERY year?”

Why not? I’ve been using an iPhone pretty much all day everyday (not really) since June 2007. Why not have the latest technology/accessories annually especially if I’m not paying much out of pocket to do so?

I understand why people want to keep whatever phone they have for years, but people also have to understand that it also makes sense for people to upgrade yearly.
 
The convenience factor of not having to deal with that makes the iPhone Upgrade Program worth it to me.
I don’t recommend the iPhone upgrade program. I’m not a credit expert but I believe it appears as a ~$1,000 loan account on your credit that you pay off after one year, which means after a few years you have a bunch of small immature loan accounts in your recent credit history. My gut says I look like a fool for needing a new spurious $1,000 credit line every year. Now I just buy it outright and trade-in last year’s model, I don’t get a loan on my credit history, I don’t need to worry about the monthly payments, and the price difference is only ~$50 more than the upgrade program if you buy the equivalent model. Maybe it works out even better if you buy on an Apple Card.
 
For me, swapping phones is a nightmare since I have to set it up all over again and that takes time and effort.

I also need to ensure every app is in its place and workflow stays the same. There’s also new iOS or new design that sometimes change my way of doing things (Touch ID to Face ID transition, or iOS 11 Control Center redesign for example).

To avoid that, I hold onto a phone for as long as possible until it becomes unbearably slow, or no longer has iOS updates.

So yeah, buying and setting up new phones is a begrudging activity, so much so I forget to enjoy the honeymoon period with it.
 
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It certainly isn't dumb upgrading this year, no matter which iPhone you currently have. The iPhone 12 series are easily the best iPhones Apple has ever made, and the biggest leap between generations ever too. Literally everything has changed with iPhone 12.
I agree that this is the best iPhone Apple has ever made! Definitely my favorite. Honestly, this should’ve been the iPhone 10. I usually upgrade every two years but going back to this design was something I really wanted. I also feel like I got a pretty good deal at $349 after trading in my 11 Pro for $450 (which I paid $500 for a year ago, after trading in my X for $400 + a $100 Best Buy gift card).
 
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For me, swapping phones is a nightmare since I have to set it up all over again and that takes time and effort.

I also need to ensure every app is in its place and workflow stays the same. There’s also new iOS or new design that sometimes change my way of doing things (Touch ID to Face ID transition, or iOS 11 Control Center redesign for example).

To avoid that, I hold onto a phone for as long as possible until it becomes unbearably slow, or no longer has iOS updates.

So yeah, buying and setting up new phones is a begrudging activity, so much so I forget to enjoy the honeymoon period with it.

Damn, I think that’s kinda torturous lol. It’s very easy to transfer everything over to a new iPhone with Apples Quick Start feature. Here is a link...


I used this method when I setup my 12 and it was awesome. I don’t keep photos or notes in iCloud anymore (lost a bunch of pics years ago), so I would usually Airdrop those to an old iPhone then transfer to my new phone later, but using quick start, it transferred everything exactly the way it was on my 11 Pro. I’m definitely using this method from now on.
 
On the contrary, upgrading after 2 years is the sweet spot. The phone depreciates more in the first year relative to subsequent years, but after the second year is still modern enough to be worth something decent as opposed to after 3 or 4 years

It’s also usually much better to skip a generation as the improvements are often very insignificant , see iPhone XR to 11.

This year is different though as it’s one the biggest upgrades ever between 2 successive generations, in the same league as possibly only the 4 and the X
I agree with you. And my percentages were probably off in that regard.
My point was that for yearly upgraders, the math can work out that it’s just a bit more expensive than waiting every 2 or 3 years. Less than you might initially think on the surface. So for some ppl, that incremental cost may be worth it for the “benefit” of getting the newest phone every year.

Again, I don’t do that (just upgraded from X to 12 Pro this year) but I can understand the OP, and others like him, who would.
 
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It certainly isn't dumb upgrading this year, no matter which iPhone you currently have. The iPhone 12 series are easily the best iPhones Apple has ever made, and the biggest leap between generations ever too. Literally everything has changed with iPhone 12.

I didn't watch the iphone announcement but with the way you describe it, I can only imagine that Tim boldly stated something crazy like "this is our most powerful iphone ever/yet!". Surely that wouldn't have happened tho.....
 
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I'll have to try this rationale with my Super-Saver Household CFO.

Wish me luck. Lol. 😂
Hey, think of it this way. It’s only roughly a $75k difference in your retirement account. I’m sure sacrificing a year or two of retirement income to have a slightly better iPhone every year (on one line) will go over just swimmingly. 👌🏻🥴
 
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Every year, I pay the whole cost upfront for the biggest, fanciest iPhone unlocked directly from Apple. This year, I will be selling my iPhone 11 Pro Max (256 GB) on eBay and buying the same size 12 Pro Max. I should get about $900-$950 for it as it is in mint condition. Accounting for eBay fees, PayPal fees, and the taxes I'll pay on the new 256 GB Pro Max, it will essentially cost less than $500 for me to upgrade.

Older iPhones obviously lose value each time a newer model is released, so I am paying only a tiny bit more than if I upgraded every 2 years or every 3 years and did the same thing. I would start saving serious money only if I kept my current phone for at least 4 years, and as a tech enthusiast I just can't bring myself to do that -- especially considering that this is a device I use for multiple hours every day.

In other words, upgrading your iPhone every year is actually not stupid or particularly expensive assuming you pay upfront, keep it in good condition, and sell the old one on eBay. Using this method, I am paying only a fraction of what those on Apple's yearly upgrade program pay. I understand that not everyone is in the financial position to do this, but if you are and are a tech enthusiast like me, I think this is the best way to do it. :)
Try this program instead. If you had bought the phone on a monthly basis, and taken the full price of the phone and bought Apple stock instead, the phone would have been free.

Fortunately I bought Apple stock many years ago and never sold it, and the dividends each year more than pays for my phone, iPads and other Apple goodies!

Gary
 
I have accepted that I will spend $50 per month to have the latest phone. My phone is never older than a year, battery issues, life, are of no concern to me. No issues with trying to sell phone, always know my cost going in. Use the Next program with yearly update. Wind up paying half price along with full tax. For me it’s the least hassle. May not work for everyone, but works for me.
 
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Signature required on all of my iPhone shipments. Problem solved
I've sold a few phones before on Swappa (and eBay a long time ago) but you always hear/read about horror stories. I've had UPS and FedEx leave packages that required signature without getting my signature. Also, the buyers could say that the product was missing from the package. There are still things that can go wrong. Yes, I'd most likely be protected by insurance and in the end things may be OK, but I don't want to go through the hassle until things get cleared up. It's not worth it to me.
 
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I've sold a few phones before on Swappa (and eBay a long time ago) but you always hear/read about horror stories. I've had UPS and FedEx leave packages that required signature without getting my signature. Also, the buyers could say that the product was missing from the package. There are still things that can go wrong. Yes, I'd most likely be protected by insurance and in the end things may be OK, but I don't want to go through the hassle until things get cleared up. It's not worth it to me.
I sold a phone on eBaY (yes I am using the old 1990s way of writing it). Guy bought it, returned it back to me which was just an empty case I included with it, then said I want a refund. I had to use forensics to prove to eBaY he never actually sent the phone back. How? I proved that the phone's weight with the case and the box is over the rate of first class postage but just the case itself is covered in first class postage which the buyer used to send back to me. eBaY gave the buyer a refund out of its own pocket and I did not lose money as I am a 20 year seller there. Avoid eBaY at all costs on high value items, ESPECIALLY cellphones. Scams "R" Us.
 
I just received a 900$ offer for my one year old iPhone 11 Pro Max 256gb on Facebook marketplace. Buyer asked where to pick up and I told him inside my local police station. He agreed and I asked for his cell number as well to confirm an hour before. So I’ll let you guys know if everything goes well. This is for tomorrow morning
 
I don’t recommend the iPhone upgrade program. I’m not a credit expert but I believe it appears as a ~$1,000 loan account on your credit that you pay off after one year, which means after a few years you have a bunch of small immature loan accounts in your recent credit history. My gut says I look like a fool for needing a new spurious $1,000 credit line every year. Now I just buy it outright and trade-in last year’s model, I don’t get a loan on my credit history, I don’t need to worry about the monthly payments, and the price difference is only ~$50 more than the upgrade program if you buy the equivalent model. Maybe it works out even better if you buy on an Apple Card.

I've been participating in the iPhone Upgrade Program since it was introduced in 2015. My credit score is currently over 800. I've also never "worried" about a monthly payment for it. It's a $60 charge that automatically gets charged to my credit card of choice.
 
I upgrade every year as well but good luck getting $900 for your used iPhone 11 Pro. I recently sold my iPhone 11 Pro 256 on swappa for $720.
I got 600.00 for trading my phone into Best Buy and used that towards the iPhone 12 Pro which pretty much means most of the new phone is paid off already.
 
My situation is better, I think. You’re saying you would pay less than 500$ for the upgrade after you sell on eBay but I would be satisfied with the bottom storage this year 128gb. I too have the 256gb but I didn’t need that much and the base of 64gb last year was too small so I was forced to go to 256gb. Heck, if I got 900$ for mine the difference would be 200$ plus tax plus a 40$ Apple case.

ebay is a lot of fees I’m guessing? Have you tried swappa? What’s your experience been selling? Just eBay ?

Ebay fees can be only £1 if it is timed right. I paid just £1 to sell my £1300 MacPro. PayPal would be the largest cost item.
 
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