I've heard the Super 8s, 9s, Xs, and O/96s with Shindo gear. Have to say the Orangutan series do not share that close of a sound with the Gibbons. Both series are fantastically musical for sure, which is why I own the 9s. But I'd describe the O series as the opposite of analytical, in that they draw you to the heart and soul of the music, plain and simple, while still sounding modern, very resolved and extended, and flat out fun - but they need some room to breathe and good placement to get that big sound to be as linear as possible (of course this depends on your room).
The Gibbon 8/9s are your more "outwardly conventional" speaker (a la Art Dudley), easier to place, work better for smaller spaces, are more linear and have better imaging, soundstaging, and bass is tighter and leaner, less voluminous than the Os... until you get to the Gibbon X, which I would not characterize as bass lean. The Gibbons are also honest to the music, but also give you the ability to enjoy the analytical side a bit more. I might say that the Gibbon series are more versatile with different kinds of music, but I haven't spent enough time with the O's to say this with certainty. I could easily live with the O/96s. Very easily. Or the Xs, for that matter.
One thing for sure: If you get a chance to check DeVores out, you'll likely get hooked.