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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-
Also, it's a built in screen /iMac - so will always have it's head on...if I've understood.
It will but you don't have to look at it. Turn it to face the wall or something.
Several people have suggested VMs which would be great with Windows but getting Mac OS to run as a VM can be tricky.
The shared drive would be fairly seamless, the change in how your father-in-law uses the computer is he would need to run VNC Viewer (or similar) to get a window on his old machine rather than walking up to it.
Microsoft Entourage
That seems to support IMAP. I'm assuming his primary email store is on the local machine so it's a multi-stage process. Start by moving his email provider to one that supports IMAP (if not already). Then move all the email from his local machine to the IMAP store. Then you can in theory run a new email client on the new machine pointing to that same IMAP store. I've done something similar for my father but he is only 80 and I did it a couple of years ago so had it slightly easier.
jellybaby
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?