The Harrowing Journey From Tiger to Snow Leopard
Unlike most Apple users, I didn’t make the quick jump from Tiger (10.4) to Leopard (10.5). Mostly because I’ve learned the hard way not to be the first in line for upgrades. And when I read about the changes they were making, I thought “I’ll wait until they work out the kinks.” And then they announced Snow Leopard (10.6) and touted the $24 upgrade but, if you looked close at it, that was only from Leopard to Snow Leopard, where little was changed on the service (but much under the hood was redone). A little looking and I found that I had to get the Mac Box Set with 10.6, iWork, and the new iLife, which I wanted anyway. And lots of my tools that wanted to use only worked with Leopard on up anyway. So Snow Leopard it is.
I ordered my Box Set and waited for Amazon to ship it (it was $20 cheaper there and no taxes. Yes, I’m that cheap!). When I got it in my hands, and got ready for the upgrade . . . I did a backup first. SuperDuper is my friend. Before this process was over, it became my lifesaver.
So I stuck the Snow Leopard disc in, and told it that I wanted to upgrade. The machine rebooted, the Snow Leopard install came up, and said it was starting and then . . . it quit, telling me that there was not enough room left on the drive. Which was very possible — there was a lot of junk on that drive. So I took the disk out and rebooted, thinking I would remove some more junk and then do the upgrade. And then it happened . . .
The machine wouldn’t boot.
My Mac would start up just fine, give me the Apple logo and then shut down. I put the Snow Leopard disc back in and that didn’t boot either! A little research showed my assumption about it booting from the DVD drive if it couldn’t boot anything else was wrong — instead it just stops. You have to hold down “C” during the boot sequence to get it to boot from the DVD drive. I went to find my Tiger install discs and booted with that. I went to run the DiskUtility and did “Repair” but it said it couldn’t. Arrgggghhhh.
I tried the DiskUtility with the Snow Leopard and it wouldn’t even Repair it — it was not a Snow Leopard hard disk!! Arrggghhhh again!
Now I had a choice. SuperDuper makes my USB hard drive bootable. I could boot off of it but that doesn’t solve my problem — the boot info on the hard drive was messed up. If I booted from the USB drive and removed enough stuff to make Snow Leopard install. But, still, nothing can repair my drive. My data was safely backed up and I know that I didn’t need it all anyway and, with SuperDuper, I can go and copy the files that I wanted off of it anyway. So I took a leap and erased the drive.
You read that right. I wiped the drive clean with the Snow Leopard installer and installed from scratch. Of course, the installer was more than willing to do that.
After that, things went mostly well. I copied our Music and Preferences folders over and Safari, iTunes, and Mail all saw the changes and updated their databases. The copying part took a while, but after that it was all smooth.
But I had lots of problems with MacPorts. Emacs.app needs some manual guidence , Python2.4 has some weirdness, and PostgreSQL/PostGIS are always a pain to install. But I got them going.
A clean install was a good thing — it got rid of the junk and I was able to move just the files that I needed. And, thankfull, SuperDuper demostrated that it’s worth 10x it’s $28 price tag.
So do your backup kids.

I’ll second the vote for SuperDuper. I used it to upgrade the hard drive in my old G4 Powerbook this past weekend (needed more space!). I also just upgraded my OS, but only to Leopard, since I can’t run Snow Leopard on the G4.
I’ll also agree that backups are your friend! I need to get another (larger) external hard drive so I can start using Time Machine now that I have it.
Knightsabre
I’m going to get a large external drive for Time Machine, too, but I’m also going to keep my SuperDuper backup around, too. They are different backups for different goals.
Most definitely. I’m doing the same with my old 80GB drive, though I did put it in a USB case I had lying around. Easier to grab something if I need it that way, I figure.
As far as large drives are concerned, you can get a 2TB Western Digital drive for less than $300 now…and I think they still have a 2-drive unit that gives you mirrored 1TB drives, if you want redundancy…at least I think I saw one on the shelf at Best Buy the other day, anyway.
[...] my clean install of Snow Leopard, I vowed I would be better at cleaning up after myself. I would delete files that I know longer [...]