I really have to try these at some point, the 660S is one of my favorite tunings in a headphone and my only complain about it is the bass extension, which the S2 apparently has fixed.
I have the Clear MG, and I already think the original HD660S competes with the Clear MG in a few areas. 660S midrange and vocals are better (to my ears), more natural timbre and surprisingly I find the soundstage height is taller on the 660S. And since the S2 has better bass extension, fixing basically my only complaint about the original 660S, I'm willing to bet the S2 will get really close to the Clear level of technical performance.
For your first statement: yep. The S2 is a clear improvement across the board, but most clearly in two areas: actual bass extension, and actual treble, both of which the 660s (despite being my favorite headphone at the time) lacked.
I can also provide a comparison to the Clear Pro (as far as I know, the same as the OG except with red and black colorway). Personally, I'd take the 660S2 every time. It has all of the charms of the Sennheiser 6 series, but with improved dynamics. IMO the dynamics are the only thing about the Clear that sets it apart- they're pretty amazing, especially at first. It quickly gets fatiguing though, at least for me. Something about the way it does dynamics makes my ears literally tired lol. With the S2, the dynamics are almost on a similar level, but with zero fatigue somehow. The Clear also soundstages very strangely. It feels like there are two bubbles to either side of your head, very rounded and to me somewhat unnatural. The S2, while more narrow, feels more natural to me.
Comfort wise, its not even close to the 660S2. I found the Clear Pro wholly uncomfortable. It felt sort of like I had a cage, or some sort of odd helmet on my head. The headband was almost unbearable without some sort of headband pad cover. Those pads are sort of a joke too, they fall apart so quickly even with care taken. And spare sets are pricey of course.
I think the Clear is one of the more overrated headphones out there, so maybe I'm biased. In short I think the 660S2 has excellent dynamics with good bass extension and treble energy, mixed with everything that's great about the Sennheiser 6 series. They will last you forever if you take care of them. The Clear have the best dynamics I've ever heard, but they're uncomfortable, fatiguing, and I'm not confident their build would last the test of time.
While I feel like the $600 price tag is a bit much (would have preferred they launch at $500 like the 660s), in a world where a Focal Clear OG costs $900+ the price is fair IMO. The Clear are way over priced I feel. The Elex at $750 is also over priced, but a much better price than the Clear.
Price is a whole different discussion. Are the 600/650 under priced at ~$300? Are they about right? In my experience and from things I've listened to all the way up to $2K, they are under priced and a deal for what you get. If they are priced right at their value, then things like the Clear are absurdly over priced IMO.
I think the S2 will drop to $500 soon enough. As much as I endorse it and think its almost a perfect headphone, I think waiting is the smart play if you have self control haha.