I've found in this hobby that context matters. I see you joined this site less than two months ago and have posted only in two threads so it's a bit difficult for us to understand where you're coming from. I see also that you're trying to build your own iem which is probably a very different mindset from us.
That being said I have auditioned a fair number of speakers now since my Chord Dave works even better on a full speaker setup and for anyone to compare any sound to a speaker without elaborating on which speaker specifically you are referring to is extremely difficult for me to relate to. Speaker sounds vary hugely, from floorstanders to bookshelves, carbon fibre to paper, multi crossover to single driver, high efficiency to low, rear ported to side, and so on and so forth.
I also have a tonne of experience with dynamic drivers now, as I own the Utopia, the HD800/S, HD650/600, and many more. The w900 sounds closer to these full size cans than the w500 did. The w500 seemed to be a guilty indulgence, almost going for an audeze-like deep bass (but not quite planar depth), whereas the w900 goes for more classic dynamic strengths- fast, clean, resolving.
Perhaps you could raise your points in the w500/w300 threads if those are the iems you're referring to. Then owners of those iems could chime in. I think the w900 is quite different- better, in my opinion.