Any time soon, Mac OS X 10.7 ("Lion") will be available for download from the Mac App Store. With Apple's website listing down over 250+ new features, it's sure to breathe new life into your Mac OS experience. Should you upgrade? I think the question is whether or not you should upgrade, but when.
Basically, if you're using mostly apps that come bundled with the current Mac OS (also called "Snow Leopard"), you should be able to hit that download button and go on and install with little or no issues.
If you're using any third party hardware or software--yes, even if it's from Apple--it's probably best if you check the hardware or software vendor's website to see if they have tested their product to run with 10.7. And then you can install.
If there's no word from the manufacturer, and your business is dependent on that piece of software or hardware working, wait before you upgrade. Most likely you'll be fine, but I'd wait for other people to see what happens before I make the leap.
What could possibly happen? Your printer may refuse to work, or the printer driver may not print properly. Really old software may refuse to launch at all. In the case of FileMaker, the last major update prevented non-english versions of FileMaker from launching unless you tinkered with some system files.
Lastly, when you're sure everything you have is compatible with 10.7, make sure you back up anything you can't lose before you install. Make a copy of your backup, and put it somewhere safe. Then, install Mac OS X Lion, and enjoy!
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