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Have you considered leaving the 2008 iMac as it is (no software updates) and running it headless? Connect to it with VNC or similar from a newer Mac for everything else and use a shared network drive for moving things between them when needed?
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You would also be able to run Snow Leopard in a VM on a new Mac.
Migration Assistant should work fine between the two Macs. I don't think there's any risk of harming the old one.
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You can run 2x versions of OSX, either as a dual boot, or window in window (or what ever it's called) no windows required.
But, it only worked twice for me with Mojave and Catalina as dual boot. And this is also to run legacy software.
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nice circa 2012 iMac
I have a 27 incher sat next to me right now. SSD upgraded... It's been sat there for a year now and not been turned on. If you'd like me to remove the layer of dust and take a photo I'm sure I can be persuaded.
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Get an iPad for him to do all new web browsing/email requirements and leave the computer he works on as it is.
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Get newer Intel-based iMac (not a new 24” M1 model), buy a copy of Parallels, install the most recent version of OSX that supports AppleWorks 6, set it to ‘Coherence’ mode: fanny’s ur aunt.
This’ll run the antiquated software in question as if it were a native app, with all saving/loading of files done from the same Documents folder or wherever he currently keeps everything.
I did something similar for a client years ago; ancient property management program coded as a mind-bogglingly complex assemblage of Microsoft Access 97 macros, which would only run on Windows XP. His 15 year old Dell desktop finally died, so I migrated everything to a 27” iMac running XP and Access 97 in Parallels, and you can’t tell that it’s not a native app.
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He keeps the iMac for appleworks 6 and gets an iPad for internetting.
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Right, got a bit of a legacy Mac issue I'd appreciate some guidance on.
My Father in Law (87 - but still working as a building stone consultant) has a conundrum. He has an 2008 IMac that is still running Snow Leopard. Why? Because he LOVES AppleWorks 6. Literally all of his technical drawings / graphs (1000's) have been drawn in this program and he's still creating more. He is too old to learn a new thing now, and my understanding is that a like for like replacement doesn't really exist anyway.
The problem is, websites are increasingly not able to run on Snow Leopard - but AppleWorks doesnt work on any newer OS. So he's getting in a pickle when emails ask him to provide meter readings, or pay bills - and the webpage doesn't load. This is happening more and more frequently.
He's also very worried (and not without due cause) that if I get fiddling I could break everything.
I think I've found a work around, where by we can run a more recent OS, and use a Windows emulator to run a windows version of Appleworks - I've got this working on my misses new Macbook (quite proud of myself).
But, he still doesnt want to plunge into updating his old Imac - for fear of it catching fire, so the solution is to buy him a nice circa 2012 iMac, that can run Catalina, and then migrate things over.
So - the actual question is - how easy is it to migrate from Snow Leopard to Catalina on two separate iMacs - and would the old iMac still be useable, in case anything goes amiss. Basically - I'm only allowed to do thigs that guarantee his old computer still works as it does now - in case I mess up the new one.
Any advice appreciated.