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I usually upgrade when I feel like it - sometimes I could go annually, other times every 2 years. I currently have a 15PM (upgraded from 14P) and don’t really see a compelling reason to upgrade this year.
 
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I gave up doing that after the iPhone XS Max series. Every 2 years for me right now, possibly even three if im not blown away by anything on this years iPhone. We dont have the same kind of incentive programs in Canada either though for yearly upgrades. We have 2 year bring it back contracts through our carriers though
 
Buy New iPhone,

Trade in iPhone same or next day at Apple.

No hassle, maximum value back as far as trade in’s are concerned.

Usually you get 50-60% of the value back.

So it costs me £500-£650 per year for the newest iPhone.

That’s £41-£55 a month for the device that I use the most, for business and personal use.

At the moment, something I can afford to have rolling per month to always have the newest device - but more importantly - a constant refreshed battery.
 
Well, my wife and I have been upgradin’ our iPhones every year since the iPhone X, always buyin’ ’em straight from the Apple Store, no carrier strings attached. We usually turn around and sell our old ones lookin’ like new on local sites in the country we live in over in Europe, typically takin’ about a 20% hit off what we paid. We always manage to recover at least 80% of what we spend.

I don’t get why some folks are okay with only gettin’ back 50% of what they paid. 😅 The way we do it each year, it’s like ‘rentin’’ the phone for about 21€ a month—seems pretty reasonable to me.

I’ve always gone for the Pro Max since it first came out, and she sticks with the regular Pro. Right now, we’re both rockin’ the white titanium, and we’re plannin’ to grab the iPhone 16 pro/ pro max in the same color, both with 256GB.

When I had the 14 Pro Max with 512GB it just didn’t pay off—seems like most folks don’t care much about all that extra storage since everyone’s usin’ the cloud these days, so I lost quite a bit of dough resellin’ it when it had more than 256GB. Maybe in the comin’ years, 512GB will be more in demand as tech improves and file sizes get bigger.
 
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I'm with Sky Mobile in the UK. Every year I buy the latest handset on finance (device only - I have a separate pay as you go SIM). Once the new phone is delivered, I sell the previous year's handset. Normally this leaves around £100-£150 left to settle the previous year's contract as I've already paid off a chunk of the contract from the monthly payments.

So it costs me around £100-£150 a year to upgrade.
 
I'll probably skip this year's 16 lineup. I'm quite pleased with my 15PM and don't see a reason to put extra $ on the new model. My laptop is also running great - been rocking the base model M2 Air 15' 4 months now and also I don't find a reason to upgrade it. My AWU2 is also rocking pretty well. I would maybe think of upgrading my AirPods 3rd Gen, since they run out of battery pretty quick, but apart from that my current lineup is solid and performs at top level.
 
When I bought the 14 Pro, I was planning to keep it for a couple years but the battery was so abysmal after a year that I decided to upgrade to the 15 Pro. USB-C was also too enticing. In my case, I just sold it to a guy camped outside the Apple Store for cash and got more than what Apple was offering. Very easy.
 
I buy a new phone and if my previous phone was an iPhone my wife takes that one and sells her old one, if it was an Android it means she’s already on last years model from when I switched to the Android in the first place and then I sell the Android.

Been switching phones more than once a year on average since the first iPhone was released and I buy the phones whatever way costs the least amount of money. If my cell provider will give me a deal on my phone for locking in the plan I already pay for during the next 24 months I will do so otherwise I buy them outright.
 
Well, my wife and I have been upgradin’ our iPhones every year since the iPhone X, always buyin’ ’em straight from the Apple Store, no carrier strings attached. We usually turn around and sell our old ones lookin’ like new on local sites in the country we live in over in Europe, typically takin’ about a 20% hit off what we paid. We always manage to recover at least 80% of what we spend.

I don’t get why some folks are okay with only gettin’ back 50% of what they paid. 😅 The way we do it each year, it’s like ‘rentin’’ the phone for about 21€ a month—seems pretty reasonable to me.

I’ve always gone for the Pro Max since it first came out, and she sticks with the regular Pro. Right now, we’re both rockin’ the white titanium, and we’re plannin’ to grab the iPhone 16 pro/ pro max in the same color, both with 256GB.

When I had the 14 Pro Max with 512GB it just didn’t pay off—seems like most folks don’t care much about all that extra storage since everyone’s usin’ the cloud these days, so I lost quite a bit of dough resellin’ it when it had more than 256GB. Maybe in the comin’ years, 512GB will be more in demand as tech improves and file sizes get bigger.
I think the resell vs Apple trade-in decision is pretty unique to where you live and the dynamics of that local market. I could see how in certain countries outside the US, the resale value could be much higher / less of a discount vs new-price, especially if it's only 1yr old and you keep your phones in good condition. In the US, there's a lot of secondary sales / lot of supply of used phones and it's a fairly liquid market, so the "market price" is generally pretty established, especially after so many years of historical precedent. If you live in a place where the dynamic is such you can get ~80% of the new price for a 1yr old phone with little risk for being scammed/robbed, I think that's a no-brainer to sell vs trade-in.

And on storage upgrades, 100% agree, this is an area where across all Apple devices, you get significantly less value for storage upgrades. Whether that's iPhones, iPads, or Macs... speaks somewhat to the often-criticized Apple pricing for its storage upgrades, that once an item is used, you usually get very little credit (either from Apple directly via trade-in, or in the secondary market).
 
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last few years I just trade in to apple for their offer.

it used to be that you would get a decent chunk more selling private on craigslist/marketplace. but I find, at least in the nyc area, that the second hand market is pretty saturated and you deal with tons and tons of lowball offers for less than what apple would give, and then after having the ad up for a few days you net like 50-100 dollars more

the trouble and time no longer seems worth it to me for that amount more
 
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I'm with Sky Mobile in the UK. Every year I buy the latest handset on finance (device only - I have a separate pay as you go SIM). Once the new phone is delivered, I sell the previous year's handset. Normally this leaves around £100-£150 left to settle the previous year's contract as I've already paid off a chunk of the contract from the monthly payments.

So it costs me around £100-£150 a year to upgrade.
Have you seen this years values ? Not sure you'll get that much upside this time - but good luck.
 
yeah value isn't as high as previous years. set to sell my pro max 256GB for £713 after some failed issues with eBay
 
I’ve always used prepaid plans, so I don’t get any of the carrier deals. I bounce back and forth between selling on Swappa and trade-in at the Apple Store. You’ll get more more money for selling your phone, especially if you have a higher storage capacity as Apple doesn’t give you any extra money for that.

But I get the base storage, and I’ve gotten to the point where I’d rather pay the extra ~$100 versus selling online to not have to deal with taking photos, creating the sale post, deal with people bargaining, packaging the old phone up, going to the post office, hoping it gets to the seller with no issues, and worrying that the buyer will try to will scam me. I just go into the Apple Store, give them my phone, and get the refund applied to my new iPhone purchase in about 5-10 minutes. Super easy.

It’s financially unwise to upgrade each year though, no matter which way you spin it. You’ll save significant money even by just waiting one more year to upgrade rather than doing it every year. At the iPhone 15 launch, Apple only gave you $70 more for trading in a 14 Pro Max over a 13 Pro Max. That‘s the difference of paying $549/year to upgrade annually versus $310/year by upgrading every other year.
Wow never heard of this Swappa site but it's pretty cool.. I have a iPhone 12 Pro and I need to upgrade very soon.. I might do one more battery change and that's it I'm thinking about giving it to my Fiance. Between the 15 and the 16 I can't see waiting out for the 16.
 
I have been getting the new Pro Max every year for the last 4 cycles but decided I will most likely not this year. There just does not seem to be enough change on my 15PM to the 16 PM. I could change my mind when I watch on Monday but kind of doubt it. I have 2 Apple watches a SS7 and a SS9 and plan to trade the 7.
 
I’ve upgraded every year since the OG iPhone in 2007:

OG, 3G, 3GS, 4, 4S, 5, 5S, 6+, 6S+, 7+, X, XSM, 11PM, 12PM, 13PM, 14PM, 15PM

For the first ~10? years, it was easy to resell. You got top-dollar. But you did have to deal with the occasional flake, low-baller, etc.

But after a while, resale prices started to soften a bit, and AT&T started the NextUp thing.

What I like about NextUp is they don’t want any of the accessories back (not that iPhones come with anything but a cord now, haha!!) AND it’s zero hassle. I buy the new iPhone, they send it to me with a return box/label, old iPhone goes in the box and that’s it. Done.

No, I don’t get what I would get if I paid in full then resold, but I don’t care. Don’t want the hassle. This way is easy-peasy.

YMMV, etc.

ETA: And I’m so glad we’re back in The Most Wonderful Time of the Year!! Haha!!
 
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I try to look at what likely upgrades are coming for the following year. Upgrades tend to be incremental at this point so I usually don't see a need to upgrade every year. I used to upgrade every year when the differences were greater between models and I like the simplicity of the upgrade program and it includes Apple Care.

I have a 14 Pro Max which won't support Apple Intelligence. I'm thinking there will be more upgrades next year for Apple Intelligence so am going to pick up the 16 Pro Max on the upgrade program and probably upgrade to the 17 Pro Max next year figuring increased support for AI and the usual set of camera improvements.
 
I wouldn't ever bother selling my iPhone privately on places like Facebook etc as there are too many scammers around. This year I'll be taking my current iPhone to my local Apple Store a few days after I buy the 16 to sell to them. Happy to take a loss over selling private if it means I dot get bombarded with stupid messages on Facebook Marketplace, or people knocking on my door.
 
I wouldn't ever bother selling my iPhone privately on places like Facebook etc as there are too many scammers around. This year I'll be taking my current iPhone to my local Apple Store a few days after I buy the 16 to sell to them. Happy to take a loss over selling private if it means I dot get bombarded with stupid messages on Facebook Marketplace, or people knocking on my door.
I started doing that as well. Unless I have a friend or family member who is interested in it. It's just a lot less stressful trading it in and taking a cut on how much I could have gotten for it. About 6-7(?) years back, I had a small scare selling my 7 Plus to a group of guys after dark in a dark dunkin donuts parking lot - I was almost certain they were about to rob me. It all turned out fine, but I never felt so uncomfortable in my life and decided to just never put myself in that situation again.
 
I received a favorable quote from itsworthmore.com. Anyone use them before?
 
I started doing that as well. Unless I have a friend or family member who is interested in it. It's just a lot less stressful trading it in and taking a cut on how much I could have gotten for it. About 6-7(?) years back, I had a small scare selling my 7 Plus to a group of guys after dark in a dark dunkin donuts parking lot - I was almost certain they were about to rob me. It all turned out fine, but I never felt so uncomfortable in my life and decided to just never put myself in that situation again.

There are well known scams occurring nationally where a phone advertised on say Facebook Marketplace attracts a buyer who visits the sellers home, they inspect the phone and either switch it for a dummy phone and walk away having not bought it, or they simply snatch it and run off.

Personally I dont want anyone coming to my home and I aint messing around meeting someone elsewhere. Apple Store can buy my phone at a lower price or else it lives on top of the kitchen cupboard gathering dust until a major museum approaches me in the future :)
 
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I'm not going to trade in my phone this year. But last year I sold my iPhone 14 Pro Max and used the funds to get my iPhone 15 Plus. Ended up not liking it at all, and sold that to get my iPhone 15 Pro.
 
Pre-order new phone as soon as pre-orders go live, I always do in-store pickup and schedule it for the earliest time available because I dont want to be stuck home all day waiting for UPS/FedEX (usually 8am), pick up new phone, Apple sends me trade in kit, I factory reset my old phone, ship it to Apple and I get half the money back I spent on the new one. Ive been doing this every year. In all the time ive been doing this, Ive only had my trade in device stolen once. Apple contacted me and honored the trade in value. Other than that, never had an issue
 
I wouldn't ever bother selling my iPhone privately on places like Facebook etc as there are too many scammers around. This year I'll be taking my current iPhone to my local Apple Store a few days after I buy the 16 to sell to them. Happy to take a loss over selling private if it means I dot get bombarded with stupid messages on Facebook Marketplace, or people knocking on my door.
To be fair these days you don’t always get more on eBay or other sites than trading in anyway
 
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