Is It Time to Update Your Operating System?

Mac OS XI spent the weekend updating my Mac (s aapl) to OS X 10.6.1 Snow Leopard. It went well, thanks to a little planning and a lot of patience. Windows (s msft) users are facing the decision as to whether and when to upgrade to Windows 7. Here are some questions to consider when you’re faced with an operating system upgrade.

Is It Worth It?

I’m generally not in a hurry to rush out and buy the latest and greatest OS. It’s always worth reading the reviews, and following reports of bugs. In this case, it’s been a while since Snow Leopard came out, and there’s already been a .1 maintenance release that seems to have dealt with most of its known issues.

Snow Leopard is, by all accounts, not that heavy on new features, but it’s also relatively inexpensive. Most of its advantages are under the hood, with 64-bit processing and better memory management. But one feature caught my eye: the ability to synchronize the Address Book (including pictures) with Gmail (s goog) or Google Apps — a feature that’s been around for a while, but which, for some reason, was previously only available to iPhone users.

Can Your Hardware Handle It?

This is an important consideration. Windows, in particular, is notorious for increasing its memory and disk space requirements with every release. And with computer prices falling all the time, it’s often tempting to just buy a new computer with the new OS pre-installed. But I decided that my Mac could work with the upgrade.

Is Your Software Compatible?

Planning for an upgrade made me realize just how much outdated and unnecessary software I had accumulated on my hard drive. Luckily, a couple of sites have compiled lists of what works, and what doesn’t, under Snow Leopard. I looked at several of them; I found this one particularly useful. It even has an application called SnowChecker that can be used to find what programs you have, and display information about their compatibility.

When you discover programs that are listed as incompatible, you can either find an upgrade (sometimes a beta version), switch to an alternative app that is compatible, or decide that you don’t need the functionality it provides.

Do You Have Backups of Everything, In Case Something Goes Wrong?

When preparing for major upgrades, I probably spend more time making sure that all of my data is backed up than I do anything else. Of course, I use the OS’s built-in tools like Time Machine, and I store multiple copies of customer data on an external drive, in the cloud through Dropbox, on my smartphone through Missing Sync, and on my company’s development server (which itself gets backed up). But it never hurts to make manual backups of really irreplaceable data, so — for example — I made backups of my address book in VCF, CSV and Address Book Archive format. You might think that I’m overdoing it, but I felt that the time was definitely worth taking after learning of Sidekick’s data loss and an apparent bug in OS X relating to guest accounts that could cause it to lose data. As Kevin over at jkOnTheRun says: “Services fail…what are you doing about it?”

Do You Have the Time to Plan and Execute the Upgrade?

Of course, doing all of this takes time, which is why I prefer to undertake projects like this after business hours. Even if it means missing a beautiful fall weekend. That way, I don’t have to interact with clients or put out fires, and being offline for a while won’t make a difference. I picked up a couple of good books at my local college bookstore where I bought Snow Leopard, and got to page 50 of Terry Pratchett’s “Nation” while waiting for the installation, so it was time well spent!

So far, I have been extremely pleased with how much faster many of the programs I use run under Snow Leopard, especially those that are available in 64-bit mode. And I’m happy with many of the OS’s new features. So for me, the time spent has definitely been worth it.

Have you upgraded to the latest operating system? How has it worked for you?