Hi,
SNAP. I'm in EXACTLY the same position.
After looking iMacs over, spec wise, and looking at my crystal all, I think your best bang-per-buck for a LONG term solution is the 27" iMac 2019 (after all, anyone like us who kept on with an MBP 2012 for 10 years is a long term kind of guy:-} ).
That's assuming you can afford to pay the +/- $2k to get a one and upgrade to top end specs: i9 9900K CPU, >= 64GB RAM, >= 1TB PCIE SSD + SATA SSD and ideally the Radeon Pro Vega 48 GPU.
If not, then slide on downwards/backwards to 2017, then to 2015.
I think you are wasting your $$$ by getting anything older/cheaper than the 2015.
In terms of a solid workhorse.
I did a table looking at the changes in CPU (speed and cores) and GPU.
Then looked at potential for upgrading/repairing the components.
The iMac 2019 is the sister to the MBP 2012: only real difference is no battery, and you CAN replace the CPU in the iMac.
And OK, a LOT more powerful.
All of the range from 2015 to 2019 have USB 3.0 and Thunderbolt. (2015 only 2.0, after that is 3.0).
As you go from 2015 to 2017 to 2019 you get a gradual and steady increase in performance, if you compare Apples to Apples.
As in compare the Standard model in each case to each other, or the top model.
But I think if you look at final price to you, it's worth it to spend the extra to get a high end 2019 because THEN you get abut the best Intel Mac that was made: forgetting the new Mac Pro for now (and it's REALLY expensive in any case).
Is good to try to get as new as possible, because all these 3rd gen iMacs are going to start being caught out by Apple shutting out Intel Macs.
Look at the time from release of a new OSX to end of support: is roughly 5 years.
On our MBP we stretched it to 10 years, but Catalina is pretty well as high as we can go.
And now Apple is really turning away from even ATTEMPTING to support Intel based apps.
So I think this is your last chance at a non-ARM Mac.
At a Mac you CAN upgrade, and have it run LOTS of stuff.
Like Win 10/Linux on either BootCamp on a VM etc etc.
I see the difference between a highly specced out 2019 and a relatively cheaper 2015 as maybe $500 or a bit bit more.
Again, comparing apples to apples.
And that extra, whatever it is, is what you are using to help keep the new machine going strong for +/- 5 years.
I suggest you decide on a base spec for your iMac, in terms of for a given year, the CPU, RAM, GPU and storeage.
And then search eBay to get an idea of prices.
And for say a given 2019 supplied as-is, add in whatever it would cost to upgrasde to your spec.
And do that for 2017, and 2015.
As in get good numbers for the RAM and SSD costs to upgrade.
Even for CPU's.
Then look at the ballpark number for 2015, 2017, 2019, and see which one you're happy with.
In UK, you can get give yourself a maxxed out 2019 iMac for +/- £1,900.
Is usually better to buy one with the GPU/CPU you want, and then upgrade the RAM/SSD's yourself.
Although with the 2015, I think all the CPU's for that are not so expensive.
But the high end Core i9-9900K for the 2019 is a lot to buy on its own: £500 new, maybe £350-£400 used.
Is still a VERY good CPU though: 8 cores, and fast.
If you're short of $$$, then in theory you can upgrade a 2009/2010, but it's a bit like the MBP 2012: stuck with USB 2 etc etc.
Plus the Retina screen is really nice, which comes in at 2015.
Plus I think anything older than 2015 is going to lose the chance to stay "current" with an OSx before the >2015 iMacs do.
The 2015 and 2017 use the same socket/chipset: LGA 1151/z170. I THINK you might be able to upgrade the CPU's to same Core i7-7700K 4 core on all of them. In any case, they are all at 4 cores.
But the 2019 has a DIFFERENT socket/chipset version: LGA 1151 rev2/z370. You CANNOT use anything else than Coffee Lake in it. And for 2017, you cannot plug in a Coffee Lake into them.
If you can use 6 or 8 cores, then 2019 is your bet. That's a large part of me picking the 2019. And you can get up to 128 GB: I might need that if I start running a lot on VM's. But I think 64GB will be fine.
Bottom line is you have a HUGE selection going from 2015 Base Model all the way up to high end 2019.
Both in specs, and availability.
But the price is not really so drastically different as I think you'll find once you work out your target models to consider in each year.
And the 2020 iMac is too expensive for what you get compared to a 2019, plus everything is soldered in.
As for the 2015 (and older), we're nearing end 2022 now, I think they're all a bit long in the tooth for someone who has just retired a 2012 as we both have.
Alan