For the past week I have not been a happy camper with my computers. An attempted upgrade of my main Mac desktop has caused a lot of heartache and pain. It all started when my daughter was visiting and was running into problems with her own Mac, which was running slowly. I suggested she upgrade to Yosemite, the latest production Mac OS. She eventually dd, and while she had to restart it from an unexpected crash, eventually her machine is now operating faster and more reliably.

So I thought I should practice what I preach and upgrade my own systems. Big mistake. In hindsight, it was my own Windows bias that was my downfall. Let me explain. When I initially setup my machine, I split the hard drive into two partitions: one for booting the system, and one for my data. That is how I have setup various Windows machines over the years, making it easier to upgrade the OS when the inevitable time comes to clean up my PC.

But Macs don’t need and as I found out don’t like to have partitioned system drives. Time Machine doesn’t back up the second partition (as I later found out), and the online OS upgrade service doesn’t know what to do with them. I went from a functioning PC to a brick in about an hour. After several phone calls and hours spent down at the local Apple store, I had my explanation, and a new system running Yosemite, with the chore of restoring my data and apps. I wasn’t entirely successful. Some of this wasn’t my fault: Apple has updated its photo app and my iPhoto libraries are stuck in limbo.

I will spare you the details and jump to some lessons learned. First, don’t partition your Mac boot drives. Use external or multiple disks if you want more redundancy.

Second, you can’t have enough backups. In addition to Time Machine, I also use SuperDuper, which makes a complete and bootable copy of my drives. That is what saved my bacon when it came to restoring my data partition.

And test your backups with some regularity to make sure they contain what you expect. I did this with the SuperDuper-created ones but not with Time Machine. Oops.

Finally, make sure you understand the progression of software tools that you will need to migrate your iPhoto library before you move into Yosemite. If you want to examine the cloud-based photo organizing alternatives, read this article that compares what Apple offers with Google, Microsoft and Amazon. My experience with using the Google Photo Backup tool, which transfers photos from iPhoto to their own service, has been abysmal: the app has crashed multiple times and still hasn’t finished copying my 7,000 or so photos from an older Mac. Now I realize that bulk uploading all these files isn’t easy. But it shouldn’t be this difficult either.

By the way, my Windows PCs upgraded to Windows 10 just fine. No show-stoppers, no grief. Of course, I can’t run any of my browser plug-ins on Edge now, but that is a feature, not a bug. Some times I miss those simpler times when we had an OS that I could actually understand on my own.