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Had the S2 for five years and upgraded to the S7 last fall...and will probably keep one this for another five years. Bigger upgrades are more fun than smaller yearly iterative updates.
 
First AW was series 1. After five years the battery needed charged twice a day and microphone no longer worked. I got a series 5 now and very happy with it. I use it mostly for exercise. I will upgrade when battery starts to wane or when then ad a BP or sugar sensor to the watch
 
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I keep my stuff until the AppleCare runs out.

I do a lot of hiking and I'm the only person who doesn't have to charge their watch up half way because it's limping. I wish to stay that way!
 
I am still on my Series 3; even though it won’t watchOS 9, I plan to keep it another year until I upgrade to the AW9 alongside the iPhone 15 Pro Max.

I just bought the Watch 7 for my mom and even though it has some nice aesthetic improvements, there isn’t really any enticing or detrimental reason to upgrade.
 
I’ve had my 5 for 2-1/2 years now, and it is still working very, very well. I can’t see trading up to a newer Apple Watch for quite a while - this one is still like “new” to me. How long do y’all keep your watches?
I have a 6 I picked up at launch in 2020, they'd have to introduce something seriously special to the 8 or 9 to get me to upgrade. I figure by the series 10, in 2024, I might be ready for an upgrade. 4-5 years seems like a decent timespan for it. We'll see though, maybe they'll introduce something shiny enough to tempt me beforehand, or maybe nothing super special even by the 10 and I'll have this even longer
 
I've started with the "Series 0" in 2015, upgraded to the Series 4 in 2018 because the Series 0 was so painfully slow. I would have kept the Series 4 until this year, but I smashed the glass last year, so I got the Series 7 in 2021. So at the moment three years, but generally the plan is to keep it for at least four years, like I do it with my iPhones.
But if there is a blood sugar sensor I will upgrade, although that seems to take several years still. 🙂
 
Just got a 7 on discount about a week ago. First AW. I'll keep it until it's either no longer supported, or a new one comes out that has features that I feel I really need.
 
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I had a series 2 that's been passed to my son. I upgraded to a 7 as a big surprise gift, otherwise, I was doing fine with the 2. The 7 was a serious step up, though.
 
Until something catastrophic happens to it or it becomes unusable due to it slowing down.
Used a S0 until 2018, replaced with a S3 Hermes, which in turn physically broke (screen popped off) and was replaced with my current S5 Ti, which is holding up well save for the battery (at 82% health).

Given the high cost of the Ti watch I may just have the battery replaced...
 
I’m using the S7 SBTi since October. I’ve had two others prior. I got the S1 in June 2017 as my first AW to match with my iPhone 7. Then I got the S4 in Feb 2019 which I thought was a huge upgrade from S1.

I’ll be keeping my S7 for a few more years. The next upgrade would be made alongside my iPhone.
 
I've started with the "Series 0" in 2015, upgraded to the Series 4 in 2018 because the Series 0 was so painfully slow. I would have kept the Series 4 until this year, but I smashed the glass last year, so I got the Series 7 in 2021. So at the moment three years, but generally the plan is to keep it for at least four years, like I do it with my iPhones.
But if there is a blood sugar sensor I will upgrade, although that seems to take several years still. 🙂
I feel you. The Series 0 was sooo slow. It should have never gotten watchOS 4. It was fine on 3. As soon as I upgraded to 4 it was game over.
 
S0 for about 2.5 years, hit something and screen totally shattered.
S3 for a little under a year
S4 actively for about 2.5 years, now use it for sleep tracking
S7 for 8+ months, it’s the Ti so only very compelling new health features will convince me to upgrade
Always had AC+, so don’t care about battery life/health
 
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I tend to upgrade every 2 years.
2015: 1st generation 42mm stainless steel case
2017: Series 3 42mm ceramic case
2019: Series 5 44mm stainless steel case Hermès
2021: Series 7 45mm aluminum case Nike (It was a toss-up decision, but I want more health sensors)
 
I got the Series 4 day 1, wear it every day, workout with it all the time and it still looks & feels like new (besides a slightly aging battery). I plan on replacing it this fall when the 8 drops though!
 
I'm still on my first one, an S4 SS. Will probably upgrade to an S8 Ti this fall and pass the S4 to my son. Every 4-5 years seems like a reasonable upgrade path to me.
 
Well I guess I will be the odd guy out lol I had aw3 while a good watch I started to hate only having 8 gigs of
Memory on board so went out and bought the aw se I really love this watch does everything I want it to do I will probably keep it until it does not receive software updates anymore.
 
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I have a S4 and every year I tell myself this will be the year I upgrade. Then they announce the Fall slate and I find myself buying the new iPhone and passing on the Watch for a larger update. There’s just no motivation for me as my watch does everything I need it for still. I mean, so does my phone, but I’m a sucker.
 
I’ve been upgrading both my and my partner’s watches each year for the past three years.

I list and sell them as a pair on Craigslist or another marketplace and it’s generally worth it.

Last year I sold the pair of Series 6’s that cost $450 each new from apple for $525.

I look at it more on a monthly price:

(449*2-525) / 12 months / 2 people = $15.50 a month, per person.

Some years work out better than others. Key is to have a nice ad and price low enough to get the deal done quickly.

If Apple offered an upgrade program on the watch I’d consider it. I do use the iPhone upgrade program and upgrade every year.
 
I got the Series 6 for the blood oxygen sensor. It still works really well and does all I ask of it. I probably won’t upgrade till the battery dies unless a really important health feature comes out.

It is almost two years old. At night the battery is at about 60%. I charge it before bed then wear it at nigh in sleep mode. I probably could charge every other day, if that was important.

I got the Aluminum model. I used to have a SS case. I really love this. It feels so light I barely know it is there.
 
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