To be perfectly honest, I don't really care what Rin Choi thinks about this or that. Especially as I've never come across his talking about sound in the actual context of music. I find his discussions of all this stuff to be quite soul sapping, personally.
I'm rather indifferent toward the EX600 and EX1000, but I like the EX800ST. I also like the H3, but only when it's modded to remove the ridiculous bass Sony felt necessary to tune it to have.
The Ocharaku connection is definitely there, since it's the ex-employee responsible for the [awful] PFV-1. Really though the "Sony spirit" in this case is an antagonistic one, the one that haunted the EX700SL that I loved so much for some reason, and one that will definitely not be some peoples' cup of tea. I've been listening to their newest invention, the Donguri, which is designed to look like a pair of acorns you shove into your earholes. It even comes with a wooden acorn pendant crafted by Oak Village in their ongoing partnership with the tea house. I was especially moved when I discovered that the housings of the Donguri were made from zelkova, the same wood used on the cups of the Sony R10. Overall the Donguri has a much more natural type of sound, somewhat removed from the wholly unnatural Flat4 (or EX700SL). They're definitely carrying to torch of Sony's madder, more adventurous and inventive side these days. However their ethos is wholly different to my mind. More one of reverence for the world at large rather than a burning desire to dominate and conquer it.
I know it's en vogue and even fun to be cynical about stuff, but personally I think the portable market is in a much better state than it was a few years ago, especially compared to the full-sized headphone landscape. $100 today will get you a lot more in an in-ear monitor than it would have before, and there's just a much wider variety of different flavors and subtle variations that exist in the comparatively young in-ear market. For instance I've been trying to decide between several "neutral-ish" CIEMs like the L05QD, UERM, 4C, and NT6. After hearing them (save for the NT6), I was rather impressed by how competently tuned they were, especially compared to the world of headphones where you just don't see that sort of thing. If anything, the world of CIEMs and manufacturers pooling from the same sources reminds me more of the hobbyist speaker niche en miniature.
As for crossovers, it really depends. Sometimes they aren't executed particularly well. Other times a crossoverless design can work well, as in the case of Custom Art's dual driver model. It's all about implementation.