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Knowing little about OSX, a friend has asked me to help upgrade their machine from OS X 10.5.8 to 10.6.3; what are the risks of doing so, if any, and what is the best way to mitigate them?

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up vote 3 down vote accepted

As with any major change to an OS I'd recommend taking a backup of the machine before the migration. TimeMachine is the Apple's built in backup software. If your upgrade goes poorly you'll be able to restore from a TimeMachine backup without supplying OS media. To ensure that you have a complete and consistent TimeMachine backup I'd recommend running the backup with all applications closed. Preferably get a few different backups so you have multiple points to roll back to.

Secondly, I'd check the installed third party applications and their compatibility with 10.6, some applications might not support 10.6 and will need to be updated to continue to work. You could install a third party program that will track application that will inform you of application updates. I use, and would recommend, AppFresh for this purpose.

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+1 @Aaron Lake: Backups are only as good as they are able to be used. How safe is TimeMachine to use, and would a disk image be a safer bet, or is it unneeded? Also, this user has huge amounts of apps installed, any suggestion for how to compile a list of apps that have the potiental to be effected be the update? Thanks! –  blunders May 3 '12 at 13:07
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I'm a big advocate of doing a "clone" backup — I use SuperDuper!, but Carbon Copy Cloner is also great. The advantage is (relative) quick return to a known state. Restoration from Time Machine is generally more time consuming and fuzzy. –  jaberg May 3 '12 at 13:11
    
See updates to my posted answer. –  Aaron Lake May 3 '12 at 13:19
    
Excellent suggestion, but I'd still do a clone. –  jaberg May 3 '12 at 16:11

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