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 $500 for me to upgrade.
Older iPhones obviously lose value each time a newer model is released, so I am paying only a tiny bit more than if I upgraded every 2 years or every 3 years and did the same thing. I would start saving serious money only if I kept my current phone for at least 4 years, and as a tech enthusiast I just can't bring myself to do that -- especially considering that this is a device I use for multiple hours every day.
In other words, upgrading your iPhone every year is actually not stupid or particularly expensive assuming you pay upfront, keep it in good condition, and sell the old one on eBay. Using this method, I am paying only a fraction of what those on Apple's yearly upgrade program pay. I understand that not everyone is in the financial position to do this, but if you are and are a tech enthusiast like me, I think this is the best way to do it. 🙂
I honestly dont understand how this is a better deal. Each year you spend 500$ yes but you have to account for that original 1,000+ plunge you did when you started this.
Lets take your example and lets say you started doing this when you bought Iphone X (so that we dont go back ages)
So you bought the Iphone X for 1,000$
Then you sold it for to get an iphone Xs Max. I will get your own metric of 500$ cost to upgrade
Then you sold that for an Iphone 11 Pro Max. That is another 500$ to upgrade
And now you will upgrade to a iphone 12 Pro Max for another 500$.
So since 2017 you have spent 2,500$ to have the latest iphone out there. If we want to be fair we have to also calculate the cost of additional accessories, like cases and screen protectors since you cant share these between phones, but ok I will be generous and leave them out of the equation.
Now my situation is the following.
I bought an iphone X for 1,000$
I can sell that phone for 500 if i try but i will again be generous and say I will sell it for 400.
The upgrade to an iphone 12 Pro Max will cost me around 800 usd
In total I will have spent like 1,800 dollars or so.
I get the appeal behind always having the latest phone in your hands (i dont consider it "dumb", if you have the money and this is your passion go for it), but it is definitely not cheaper by any means.