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My late 2009 iMac 27", 2.8ghz Core i7, 16gb ram, 512gb Crucial SSD with Radeon HD4850 GPU is running macOS Mojave (thanks dosdude) like it was new. I've had it 10 years since new and has never let me down. Recently the bluetooth card has gone funky ($5 Fleabay) so I'll be replacing it soon. This model (2009-2011) is easy to open up and work on unlike the iMacs from 2012 to present. Plenty of useful life ahead. It runs cool thanks to dual SSD's inside (boot-optical SATA). They don't make them like this anymore.
 
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My iMac is Mid-2011, 2.5 GHz Intel Core i5 with upgraded 12GB of Ram. I upgraded the ram a few years ago. It's running High Sierra.

I've contemplated selling my iMac many times over the years. But it managed to stay on my desk, and at this point I've decided to just keep it until it finally goes to pearly iMac gates in the sky.

Although lately the screen has been flickering ever so lightly. Like auto-brightness is going haywire or maybe a graphics card is starting to go? I don't know.
 
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Although lately the screen has been flickering ever so lightly. Like auto-brightness is going haywire or maybe a graphics card is starting to go? I don't know.

I'd more likely so an issue with the backlight or power delivery, but you could disable auto-brightness in System Preferences to rule that out
 
Still rockin' a 2011 27" 3.4GHz and 2010 27" 2.93GHz for FCP7, waiting and hoping on a proper 1000-nit HDR Display iMac/MBP to finally migrate to FCPX for my ever-growing catalog of 10-bit HDR 4K footage.
 
Still running my late 09 iMac, just added 4 gig of ram for about $30 and it runs HighSierra like new. I was going to add an SSD but after the ram upgrade no need to.
 
I'm in the process of replacing an early 2009 24" iMac with 2019 27". Other than a failed HD which I replaced myself the 24" iMac was 100% reliable. If it could be updated beyond El Capitan I might have kept it even longer. There are some faint lines visible on the upper-left of the display which may indicate a pending problem
 
Just yesterday replaced an early 2009 24" iMac that had an SSD and 8GB memory upgrade, with a 2019 27" 24GB memory (8 apple plus 16 add-in), 1TB SSD. I had the 2009 running High Sierra (thanks to dosdude) and it's still 100% functional, just too slow to run much of what we want to do on it today. The SSD upgrade gave the old machine an extra couple years of useful lifetime.
 
Obviously everyone's usage is different! I bought my parents an iMac in 2010. They are not power users so I bought a low-end machine: i3, 4Gb RAM, 500Gb spinning drive. They still use this as their main computer without any upgrades. It's on some ancient version of OSX but does everything they need.

I have a friend who bought an iMac in 2009. It has been upgraded as far as possible and using some hacks is running a recent version of OSX. Again it's their main computer.

I'd say that any machine you buy now will be fast enough for most things for the next 10+ years (if the hardware doesn't fail). The biggest issue from a Mac point of view would be the likely upcoming ARM transition and what this might mean for the longevity of Intel Macs.
 
My mid 2013 27" iMac is just purring along nicely - I upgraded the RAM a few years back and swapped out the old rotational HDD for an SSD two years ago. Great machine!
 
I'm in the process of replacing an early 2009 24" iMac with 2019 27". Other than a failed HD which I replaced myself the 24" iMac was 100% reliable. If it could be updated beyond El Capitan I might have kept it even longer. There are some faint lines visible on the upper-left of the display which may indicate a pending problem
I have an early 2009 24” iMac that’s running High Sierra great. If you’re interested, visit the unsupported Mac section of High Sierra sub-forum. It’s really easy to do.
 
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