I don't tend to upgrade my operating system until there's compelling reason to do so. Backup for the beloved's desktop machine using Time Machine, screensharing through iChat to the beloved's dad's machine to help him learn to get around, and a couple of Leopard-only applications were the things that recently pushed me over the line to abandon Tiger.

While the issues I came up against weren't terrible, I can't say that the upgrade process went particularly smoothly, but then it turns out that I didn't follow the available advice. Not advice that apple provides when you buy Leopard, but advice you find when you're searching the web when the upgrade doesn't go well, like make sure you disconnect any firewire drives.

The first time through the upgrade hung at "About a minute" to go. I left it for more than eight hours with no progress and no log messages. I had all the data backed up, and I wasn't too concerned about losing things, so in the end I gave up and forced a reboot. I changed nothing, but the second time it managed to push through the last minute and upgrade in a reasonable time.

The first problem I now had was that the afformentioned firewire drive, on which I planned to automate backup, was not visible. I tried to troubleshoot for half an hour with no luck, then shut down, power cycled the drive, and restarted. Voila, fixed.

Next, Mail showed mailboxes but no mail and wouldn't quit without being forced into it. Another ten or so blind alleys, and I came across an article from Apple telling me to move a couple of plist files out of the way, restart Mail, and move them back. Not too hard once you know how, the fun is in getting there.

Now, after running for more than eight hours, the initial backup to Time Machine has managed to copy two and a half GB out of the 100 or so it needs to get through. Given that the default is to backup once an hour, let's hope it doesn't take that long every time (you have to edit a plist file to change how often Time Machine runs).