Well, most of the podcast hosts upgrade every year for sure… 
I am not in the upgrade every year camp per se, but I plan on getting the Pro Max 12 although I currently own the Pro Max 11 (the camera technology is what I am looking forward to). 
I’m sure that’s a fun write off they get to take.
I try to hang on to mine for at least 2 years, or until there’s a trade in deal from my carrier that I can’t refuse. I’m hoping the phones/cameras from the last couple years are powerful enough that they’ll last for some time. We’re also on an older Sprint plan that I don’t want to let go, but I imagine T-Mobile will want to clear out those customers at some point and force us on new plans.
I bought my iPhone 6s in November 2015. Still going strong and I don’t have a compelling reason to update (yet).
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How well is your battery coping. My 3 year old X is struggling.
I see no reason not to upgrade annually so long as trade-in or used market prices are good enough, or I’ve a good hand-me-down target.
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2-3 years for me.
3GS
4 (iPhone 3GS was snatched)
5
5S (I switched my iPhone 6 Plus with my girlfriend with her 5S)
7 Plus
XS
FaceID no longer works on the XS due to excessive rain in Fuji Rock last year. But with the mask on, I don’t miss it but I do miss TouchID. Other than that still rock-solid performance and battery life. Not planning to upgrade this year.
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Was going to go for the 12 (and posted here that I would) but now: meh.
I don’t need a better phone camera and the rest of the time I just text and speak. Will stick with my X for at least another year.
I live in urban areas most of the time, with no lack of wifi so 5G is not needed. (It’s probably a fraud right now, anyway.)
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Battery life has seen better days, but it is still able to last 12 working hours with light/moderate use. I generally use my iPhone for text, task managing and occasional browsing (not because I m babysitting the battery, but because I have other devices for video, web-browsing and all the other more energy-demanding functions).
If I had to use it more extensively, I believe I would have to upgrade more frequently, for sure.
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Still rockin’ my jailbroken 8Plus. Not worth upgrading to put myself back under GrannyApple’s thumb…
I buy the newest one and use until it falls apart. The jumps in capabilities are too insignificant to dive into tat rabbit hole.
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I started with a 4S that I still use on an old Sony home speaker setup for radio as air reception in the hills is pitiful. I bought a 5S that I keep as an emergency spare, loved the size! Traded in a 7 for the X I am using now. BUT, I’m really intrigued by the 12 mini. I like the smaller sizes, but love the cameras on the larger formats.
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I’m a tech consultant, so have to be pretty updated, but I’ve stuck to a pretty regular 2-year plan.
Original (dropped it and broke it about 18 months in)
3G
4
4s (remember, that was 18 months after the 4, and the camera on the 4s was quite an upgrade!)
5s
6s
8 Plus (Which was really the 7s, IMHO)
11 Pro Max
I just bought this phone in December (Bought it outright with a discount from work, also got Apple’s 6% cash back using my AppleCard! And the 8 Plus fetched a nice $300 trade-in!)
I used to be a yearly upgrade sort of guy, but I’ve managed to stay with my XR for the last couple years, as well as the S4 Watch for 2 years. The improvements between device cycles have become smaller and smaller over time and it makes more financial sense to wait every 2 to 4 years now (device performance the primary driver of decisions).
But I have to say, that iPhone mini is looking really good 
My history is getting longer
iPhone 4s purchased in 2011
iPhone 5s purchased in 2013
iPhone 8 purchased in 2017
I’m looking at maybe next year or more before I replace my 8 as it’s doing just fine for me. I won’t replace it until I have an overriding reason to do so. Things like a major repair needed, or a major new killer feature I just gotta have or I’ve run out of space.
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I’m going to replace the battery in my iPhone X and use it another year or two. I use my phone to track bike ride miles, listen to podcasts/music when walking/driving and to take photos. Mostly share the photos on Instagram so no need for the latest and greatest for those tiny, ephemeral images. Even at larger sizes these photos are better than anything I would have taken 10 years ago. Oh, and it’s my internet source as a hotspot.
For the money, I don’t see the benefit. I think Apple has done an excellent job marketing the new phones every year and certainly they are improved each year. But not nearly enough to convince me to spend that kind of money.
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We buy through Verizon where we have a two year contract. So we keep the phones for at least the 2 year term (sometimes longer) before buying again.
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I will be closing the poll in the next 24 hours, if you have not voted, please do so 
I am already amazed by the response to the polls.
I was a 2 year upgrader before I joined the Apple Upgrade program. Now the annual upgrade is an easy decision since my monthly cost hardly changes. We actually think our cost might drop a couple dollars this year from what we have read. I would be fine every 2 years or even 3 if I was paying in full for the phone. I don’t pay in full because we have a small family business and we provide 4 of us with phones, so it is just easier to cover that cost as our revenue comes in with the Upgrade program.
With rare exception, I replace tools when they break, but I understand I’m not all that fashionable. I mean, I’d like to buy a new truck, but my '99 Tacoma just won’t die. Same with my '11 iMac and my iphone 7.
¯⧹_( ツ)_∕¯
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You’re not alone. Not purchasing every new shiny that catches my eye has allowed me to avoid a car payment for more than 30 years. And be able to purchase a new iPhone, iPad, or Mac when I need one - which is not that often.
With the exception of their laptops Apple’s hardware can frequently remain useful until it becomes obsolete.