Well, after some more listening and comparisons, I have concluded the following - which echoes the few last comments on this thread:
With the Woo WA2 (OTL), the 650 has a sweetness that the 600S doesn't possess. In comparison, the 660S sounds a little bit cold. It's still quite good, but not as good as it should be. So, avoid the 660S if you have an OTL.
With the Sony ZX300, balanced, the 650 doesn't sound bad, but is not very exciting. It's a little flat and lacks separation. The 660S, on the other hand, is majestic, powerful, and fun. I'm sure that the lower impedance helps a lot.
I love them both, but since these days I'm only listening to the ZX300, the 660S is the better choice. I bought it to work with that DAP in the first place, so it's a win.
Now, I must confess there's something I truly hate about the 660S, and it's not sound or comfort related; it's the insane length of the 4.4 cable! Come on Sennheiser, the 4.4 is mainly to be used with a DAP. Do I really need a cable that's 9 feet long?
Consequently, I'm going to order a 3-foot Michanikos cable from ZMF. It's should slightly change the sound in a good way, and will be the right length for a portable DAP.