I almost got Chocolate running on a 10.9.4 machine with all the latest developer tools (including Xcode 6), all built from source and 64 bit with the latest git checkouts (including phobos). Of course it is not within Xcode but using dub, so the biggest thing yet to do is to bundle an OSX app with dub, so far for the word almost before ;)
This looks very promising, thank you Jacob for all the hard work! I soon want to start to write a tutorial including a step by step guide.