Interesting thread and question. I've owned the Vandy 2CE Sigs, and more recently the Treos, and currently own a pair of Daedalus speakers. My good friend has the O/96 Devores, All great speakers IMO.
Interestingly, I think the Vandy 2CE Sigs compare more closely to the Devores than one might think, as they have that 3D, almost holographic presentation to them. The Devores when driven with the right electronics (they are very dependent on what you drive them with according to my friend, and he drives his with Shindo gear) are also smooth and holographic. The RSD Lou Reed Perfect Day Live set literally brought the legend back to life in his living room. I think the Devores have a touch more forward detail than the Vandies, which are a little more polite and have a soundstage a bit further back.
The Treos have a more forward soundstage, a little more flavor "on the nose" of the sound, if you will. I fond their detail retrieval to be excellent, especially late at night with lower volumes and you really felt like you weren't missing anything. That forward sound comes at the expense of that holographic sound of the 2 CE Sigs, though, at least to my ears. The older, sock puppet Vandersteen designs have a certain magic to them that I love.
The Daedalus speakers are also similar to the Devores, and often compared to them. The workmanship of the Daedalus is just absurd. They could be sold as furniture by Ethan Allen, they would be $20,000 a pair based on labor and materials alone. Don't let the pretty woodwork fool you, though - they have top notch drivers and crossovers and a sound that Lou Hinckley (owner/designer/builder of Daedalus) tunes to replicate what you hear when you hear live music, and to a real musician's ear. Lou's stage creations were legendary, and in fact, the aforementioned Lou Reed had a Daedalus stage monitor speaker on tour with him in his last acoustic tours. In my listening room, the Daedalus give you the detail, the smoothness of good acoustic instruments, yet none of the harshness and listener fatigue of many "high end" brands.
Hard to see going wrong with the Daedalus or the Devores. I think the Devores are a bit more fussy with electronics, whereas the Daedalus can be used with a wide variety (although quiet gear is a must as they are 96bd efficient). The Devores excel with great jazz and vocals, although they can rock out as well. The Daedalus can definitely handle all types of music. Bass extension is better IMO with the Daedalus. The Devores would benefit with a good, fast sub (Vandy maybe?).