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I keep my iPads even after they have iOS versions that are too old to use as main iPads. By then, they’re so cheap that selling or trading them gives me less value than to just use them with whatever capabilities they still have.

My 9.7-inch iPad Pro is almost 9 years old, I won’t get much for it. So I still have it. It’s also my favourite iPad ever, but that’s a different aspect altogether.
 
I bought my first iPad when they were introduced in 2010. I've had four so far, so my upgrade time is 3.75 years. Actually my last iPad (11" Pro) still works fine and I still have it.. But I wanted a 13" screen so I picked up an M4 last fall.
 
My 9.7" iPad Pro is 9 years old. I'm ready to upgrade, but I've been putting it off for almost the last two years because the iPad is purely a 'want' for me rather than a 'need'.

I've upgraded my iPhone and iMac in that time span, but I use both of those extensively every day. My iPad gets used much less frequently - maybe once or twice a week, if that. I'll eventually do it anyways though, maybe sooner than later, just because I do want a newer one.
 
I had an iPad Pro 10.5 from 2017 still going strong into 2023 when I finally gave it away due to not really needing/wanting a tablet anymore. If you all you do is YouTube and web browsing, recent iPads seem to last forever and stay speedy.
 
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I have a 2020 iPP 12.9 that has battery life issues; but not enough of an issue that Apple will allow a battery replacement. (MaxCap = 82%). Trying to decide what to do before a long trip in late June.
 
I have a 2020 iPP 12.9 that has battery life issues; but not enough of an issue that Apple will allow a battery replacement. (MaxCap = 82%). Trying to decide what to do before a long trip in late June.

Like how bad is the battery? Shorter battery life but still serviceable or randomly shuts down and goes from 100% to 0% in 5 minutes?

Personally, I like to use my old devices for trips assuming battery life’s not too awful. Having an old device lost or stolen is far less painful than losing a brand new one.
 
How many years do you generally keep your iPad Pro before you find it’s time for a new one?
No simple answer is appropriate since users are wildly different (many users today grew up being baby sat by iPads, while others spent lifetimes in Mac OS) and iPads/usage has evolved over time.

Also Macs and iPhones have evolved over time: we now have powerful low end MBAs competently running Mac OS that are much cheaper than high end iPad Pros, and large iPhone Pro Max phones that scream out for pencil capability. So "how old" one allowed a 2015 tablet to become will likely not be the same "how old" one allows a 2024 tablet to become (even the same user).

Personally I owned a v1 iPad until the battery died, and now still own a v1 iPad Air that only gets used on airlines. I test drove both an iPad Pro and an iPad Mini intending to take one back and ended up taking them both back. Still not enough value add in 2024 tablets to make me want to use one - - because [for me] the combination of loaded M2 MBP and iPhone Pro Max obviates integrating a modern tablet into my devices usage. What I really want is for the iPhone PM to gain pencil capability. I will happily even carry and charge the pencil separately.
 
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Like how bad is the battery? Shorter battery life but still serviceable or randomly shuts down and goes from 100% to 0% in 5 minutes?

Personally, I like to use my old devices for trips assuming battery life’s not too awful. Having an old device lost or stolen is far less painful than losing a brand new one.
It runs fine; battery life is just shorter than ideal. But I have a Basseus battery pack for the flight.
I would have probably traded it in by now but I have a dead pixel and related screen issues (not a broken screen) that makes the Apple trade-in value $0. Hoping to get a battery replacement to fix both issues.
 
It runs fine; battery life is just shorter than ideal. But I have a Basseus battery pack for the flight.
I would have probably traded it in by now but I have a dead pixel and related screen issues (not a broken screen) that makes the Apple trade-in value $0. Hoping to get a battery replacement to fix both issues.

If the iPad has other issues apart from battery, chances are Apple won’t allow a battery replacement.
 
If it's for business, time is money, probly 3-5 years.

If is personal, until I can't stand the slowness AND there is a good deal available. My last electronic lasted 15 years. U know u need a new box when the old box cannot be upgraded further and the swap file comes on right away.
 
Even after the expiration date (whether that's 3 years or 9), convert the old iPad into a digital photo frame and it will last another 5+ years. I have four of these around the house since I'm the one that everyone in the family gives their old iPads to when they upgrade. As stated elsewhere, they aren't worth selling on eBay, but they keep memories alive and help remind you of the tens of thousands of photos you've taken since photos went digital.

I wish the Apple Photos app made this easier. I had to download a special slideshow app to do what I wanted...but it stays on 24/7 and even tells me the weather.
 
How many years do you generally keep your iPad Pro before you find it’s time for a new one?
It highly depends on when Apple is offering new models that I find more attractive than what I have. For example, I had (actually still have and use as a second screen for video conferencing) a 2018 iPad Pro (bought used in 2021), and only the 2024 OLED models made me interested in upgrading. I also have a mini 5 from 2019, and since I don’t like the mini 6-7, I still use that.

As long as the battery is good enough, nothing breaks, and no significantly better-in-practical-terms model comes out, I will keep a model as long the apps I use support it. My father kept the original iPad 1 for almost ten years, and only switched to a new model because websites started to break on the old Safari.
 
I keep my iPads even after they have iOS versions that are too old to use as main iPads. By then, they’re so cheap that selling or trading them gives me less value than to just use them with whatever capabilities they still have.

My 9.7-inch iPad Pro is almost 9 years old, I won’t get much for it. So I still have it. It’s also my favourite iPad ever, but that’s a different aspect altogether.
Does the 9.7 iPad Pro still work ok? Last time I used a 1st gen 11inch iPad Pro it drove me crazy how slow everything was. I guess just content consumption would be ok. YouTube, Netflix, etc. but even swapping between tabs was brutal. I also loved the 9.7 iPad Pro. It was my replacement to my 3rd gen “the new iPad”.
 
I got the original iPad when it first came out and upgraded annually at first. I’ve been on a three year refresh cycle since 2018 but my current iPad Pro may stretch that further.

My iPad history: iPad 1 2010, iPad 2 2011, iPad 3 2012, IPad Air 1 2013, iPad Air 2 2014, iPad Pro 2017, iPad Pro 2018, iPad Pro 2021 (still being used by my wife), and now use the current iPad M4 13 inch. Plus my wife got an iPad Air 3 back in 2019 which she also still uses.
 
I keep them long enough that trade-in values have already tanked by the time I'm ready to replace them.

My old iPads get better use given away to family and relatives.
Trade in values tank the day you buy them. The brand new M4 iPad Pro goes for like $200 or $300. To answer OPs question typically 5-6 years Ill get the best they have (just upgraded my 2018 with the M4 iPad Pro). However this will likely be my last iPad unless apple does something serious to improve the platform.

In addition to my reliability issues when using an external display there is just way too many tiny things that prevent me from using this as a serious business device. The Vision Pro is looking like a real productivity winner more and more and will likely be my portable device going forward for business, or a MBA.
 
I traded my 2020 iPP in for the M4 iPP last year. Now I'm selling my M4 and buying a MacBook due to my needs changing. Cest la vie. Goes to show iPads, especially Pro models, last a very long time.
 
Does the 9.7 iPad Pro still work ok? Last time I used a 1st gen 11inch iPad Pro it drove me crazy how slow everything was. I guess just content consumption would be ok. YouTube, Netflix, etc. but even swapping between tabs was brutal. I also loved the 9.7 iPad Pro. It was my replacement to my 3rd gen “the new iPad”.
Mine does, but I don't do "power user" stuff on it. Some web browsing, a few apps, a little simple word processing, listening to music, etc., and it's my tv screen sitting next to my iMac when I'm 'kind of' watching sports or something and don't need it on a big screen.

Apps all open quickly and work fine, but I only get about 4-5 hours out of the battery and it can't upgrade past 16.7.11. I never have a lot of tabs open in Safari, but switching between the 2-3 tabs I might have open doesn't give me any problems.
 
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