I've got as far as Mavericks. Seventy one's comments about the re-purchasing apps. is putting me off upgrading to Yosemite. Plus my Dad bought a new iMac that came with Yosemite to replace his G4 iMac. He thinks Yosemite is terrible if you are coming straight from an older Mac OS like Snow Leopard. There are a lot of changes to absorb. He thinks a lot of the bundled software has been messed around with and doesn't have the same functionality as their earlier incarnations. Plus, even with Mavericks, one no longer gets the opportunity to read what each Software update does? You either have to intall it immediately or break out and run AppStore/Updates to find out what is being downloaded.
With Mavericks I find I can't upgrade my iWorks apps that I bought on a DVD but have to download new versions from the App Store. But that means having to pay for them again. So Mavericks wasn't really a free update as it has turned out.
I think you can safely go as high as Mountain Lion and still have a good OS. Mavericks is okay if you are prepared to replace and pay for iWorks. May be worth it if you like iCoud Keychain for instance.
I'm not sure if I will upgrade to Mavericks or not. I will need to play with my Dad's new iMac a lot more before I can decide.