What do you consider when upgrading your OS?

I’ve got a four year old Macbook Pro on which I’m still using OSX 10.6.8 (two versions behind current). I have, however, used 10.7 and 10.8 at work, and while there were a few things about it that annoyed me (like the default hiding of stuff I use at home to do backups), I could also look up how to get around those pretty nicely.

I saw some of the negative reviews of Mountain Lion on the App Store, but I don’t use a lot of the features they were missing, like the four finger app swipe (I didn’t even realize you could do that). Plus, I figure I’ll upgrade one way or another, when I get my next computer if nothing else (although I plan to hang onto this one as long as possible), so now might be the time.

Any reason not to? What should I consider when making this decision?

If it works the way you want right now, why mess with that? I have 10.5 on an iMac in my kitchen, and that’s waay long in the tooth and I keep thinking I should upgrade it, but I keep seeing no good reason to. Which sounds like you, right?

I get your point, and I do agree to some extent, but if your iMac’s in your kitchen, how much do you really use it? I mean, this is my primary home computing platform. Eventually, time’s gonna catch up to the OS, and I figured I may as well “train” myself in the new stuff.

Plus I wonder if performance will be better with the newer OS.

If you want someone to say “ohnos, don’t upgrade”, I’m not that guy. I don’t find 10.7 or 10.8 tres sexy vs 10.6. They’re just this year’s flavor. I get OS-X upgrades for free via work, so I just upgrade because I must to do my job. I liked 10.6 quite a lot, I grudgingly liked 10.7, and 10.8 is also fine. 10.9 is pretty crashy so far, but I’m sure they’ll shake it out.

Whether Mr. Torvalds has released a new kernel.

Consider if your applications support the new version. And consider if you really want/need anything in the new version.

I had a major pain upgrading from (I think) 10.6 to 10.7 a few years ago. Everything seemed to get slower. I had a bunch of kernels panics for a few days until I found some webpage that told me how to fix some broken kernel extension. The VPN software I used to connect to work needed to be upgraded, and the new one had a weird bug in it that I spent several hours sifting through mailing lists and trying things before I found the fix. I had to buy a new version of Parallels, since the version I’d been happily using no longer worked on 10.6. The new version of Parallels was total shit. Moved at a crawl. Actually unusable. Never did find another good solution there, so I gave up playing the one old game I used Windows for.

Other upgrades had always been quick and easy, so I just blindly did them when they came out. I don’t do that any more.

All in all, it took probably 20 hours of my time and an extra $60 for the crap version of Parallels, and I don’t even remember if there was something in 10.7 I really wanted. When 10.8 came out, I didn’t bother. I didn’t need any of that stuff. I am planning to upgrade to 10.9 when it comes out, since the battery life savings and full-screen not being totally stupid with multiple monitors are worth the upgrade to me.

Computers are complicated. If it ain’t broke, don’t fix it.

I shudder at the thought of getting a new computer and having to learn a new OS. I think they hate us, they especially hate us old farts.