Not risky at all. Get an external hard drive or create a new partition on your hard drive. Install Mavericks on one or the other. Then you need not risk your current system at all, but you can check out all your software and give the new OS a spin.
Upgrading to Mavericks
You can upgrade to Mavericks from Lion or directly from Snow Leopard. Mavericks can be downloaded from the Mac App Store for FREE.
Upgrading to Mavericks
To upgrade to Mavericks you must have Snow Leopard 10.6.8 or Lion installed. Download Mavericks from the App Store. Sign in using your Apple ID. Mavericks is free. The file is quite large, over 5 GBs, so allow some time to download. It would be preferable to use Ethernet because it is nearly four times faster than wireless.
Macs that can be upgraded to OS X Mavericks
1. iMac (Mid 2007 or newer) - Model Identifier 7,1 or later
2. MacBook (Late 2008 Aluminum, or Early 2009 or newer) - Model Identifier 5,1 or later
3. MacBook Pro (Mid/Late 2007 or newer) - Model Identifier 3,1 or later
4. MacBook Air (Late 2008 or newer) - Model Identifier 2,1 or later
5. Mac mini (Early 2009 or newer) - Model Identifier 3,1 or later
6. Mac Pro (Early 2008 or newer) - Model Identifier 3,1 or later
7. Xserve (Early 2009) - Model Identifier 3,1 or later
To find the model identifier open System Profiler in the Utilities folder. It's displayed in the panel on the right.
Are my applications compatible?
See App Compatibility Table - RoaringApps.