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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?
jellybaby-
I'm not a computer expert at all - I just google/youtube things and hope i can muddle though. I don't really understand the above - but anything that requires him to alter how he currently uses his computer is probably a no, so some shared drive sounds tricky.
Also, it's a built in screen /iMac - so will always have it's head on...if I've understood.
Scrabble
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.