I haven't upgraded my 2008 MBP yet, but on 2 other 2013 Macbooks and my Hackintosh the Mavericks upgrade was smooth. One of the Macbooks is an Air (no retina screen) and it looks the same as it did on Mountain Lion. I had purchased Parallels as part of a bundle a couple of months ago and the upgrade to 9 was free.
I might try Mavericks on my old MBP but I'll clone the hard drive first so if it's not a good experience I can go back.
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