From Snow Leopard To Mavericks And Back Again

From Snow Leopard To Mavericks And Back Again - by David R Beebe
I kept putting off upgrading from OS X 10.6.8, aka Snow Leopard, because it was the last Mac OS that didn't try to emulate a tablet. With the promise of 10.9.3 restoring the ability to sync an iOS device's contacts over USB to a local computer, it seemed like a good time to try.

Taking nothing for granted, including the need for a possible full retreat, I took cautious baby steps. For many apps it is a one way journey without backward compatibility. I was specifically concerned with Aperture and FCP X. First, I cloned my Machintosh HD to an external USB disk using Super Duper and booted from it. From there, I downloaded the Mavericks installer from the App Store. I ran the upgrade and following updates. This turned out to be an iterative process. I had a test library to upgrade with Aperture and that appeared to work OK along with the NIK plug-ins. I have a couple of old apps that I still use frequently. RapidWeaver builds my website's main structure and JAlbum 7.4 creates each of my photo albums. Both ran fine with after an auto-installed popped up to add a bit of system software.

All ran well until I got to iTunes. The next sync of my iPhone 5 failed to update the calendar or contacts as promised. I'd never used iCloud as this is not an option from 10.6.8. A quick Google search uncovered the need to force a push of the calendar from iTunes to the iPhone. This worked and I was then able to combine updates that originated on my iMac or iPhone over USB again. I still could not get Contacts to sync so I tried the same approach. Big mistake as I lost all contacts on my iPhone. I was later to discover I also lost all of my custom ringtone assignments.

After fighting for hours to get that to work again, I gave up and retreated back to Snow Leopard and restored my iPhone from there.

While I am on the subject of iTunes, I've noticed that since 11.2.2, every time I launch it, it runs through 70+ tracks analyzing for gapless play. Another Google search and it seems there is some minor corruption in the iTunes library. The suggested path to fix it was to wipe iTunes and re-add the media back into it. WARNING - no where does it say that doing this will cause you to lose all of your custom playlists. So, another retreat to the previous backup of iTunes via Time Machine.