I think it’s wise to leave it at Tiger, especially if you’re more
familiar with that and will do tech support.

If you give him an administrator account, then the best thing you can
do is to get an external HD with Firewire and set up a complete
(incremental) backup schedule with Carbon Copy Cloner. Or maybe two:
one daily and one weekly, to different partitions.

You’re doing the right thing in giving him a Mac. Macs are more
orderly, which makes him think/work more orderly -- a little bit,
anyway.

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