Apple released the new Mac OS (operating system) Yosemite (version 10.10) a few weeks ago and many customers have called, emailed, or dropped by to ask if we are recommending the upgrade. So rather than answer the question several hundred times, let me answer it once and for all…
Installing a new OS is the most invasive thing you can do to your Mac. Every program, every accessory, and every peripheral interacts with that operating system, therefore it could potentially introduce lots of conflict. The flip side is that we are all Mac users for one reason, because Apple’s products are superior to other choices. The crown jewel of Apple’s offerings is it’s operating system. Staying current on the OS allows you to enjoy all the latest features and benefits. Oddly it also makes installing future OS upgrades easier because it’s much easier to hop from say 10.9 to 10.10 than it is to leapfrog from 10.6 to 10.10.
So my very generic - your mileage may vary - advice is as follows. Keep in mind that nothing in life is free. Yosemite may be available for “Free” from the app store, but installing it will at minimum cost you some time and it could cost you lots more. If you should need upgrades or updates to software or hardware just to be compatible, that free upgrade will now start costing you real money. Our very general rule of thumb is - If you are currently running Mac OS X 10.7 or better, that includes Lion (10.7), Mountain Lion (10.8) or Mavericks (10.9), then installing Yosemite (10.10) should be a pretty painless process. If you have something which pre-dates Lion (10.7) then I would not recommend upgrading to Yosemite because many programs which run on Mac OS 10.6 and earlier do not run under 10.7 and later. Also keep in mind that the age of your computer matters. Generally speaking a computer more than three years old is considered “old” and may require hardware upgrades in order to properly run the new OS.
Regardless of which OS you have, one very helpful resource is http://roaringapps.com. This is a web site which hosts a database of compatibility. There you can look up specific Apps you run and see what other people in the Mac community have to say about their experience with that program. As for my own personal Yosemite upgrade, I was of course running the latest version of Mavericks prior to installing Yosemite. The install went fine and, after restarting, one important program I run called QuicKeys no longer functioned. I also had problems with one of my printers (a Dymo LabelWriter) which ceased to function after Yosemite was installed. Thankfully a few updates and downloads later and I had restored functionality to both. That kind of experience is normal when upgrading the OS. In the end it only cost me a few hours of downtime.