"What do the MWTs most resemble as far as headphone brand/style?"
Probably the more neutral sounding ones with flatter frequency response, which I have seen several models of the brands you mention have been measured to achieve.
But its is really hard to compare speakers to headphones because they are so different. Room acoustics play a big part usually with speakers but not with headphones.
OHMs are bottom ported and most I have heard with no bottom plinth can interact strongly with floors, especially those in upper levels built with plywood as is typical in most homes. I use a slate tile under each of my 100s to tame that in my second system where it occurs. The 1000 series OHMs all have the solid wood plinth below which I think is a good thing to help inherently tame that.
I have always found many smooth and hard roon surfaces, hard wood flooring in particular to be quite lively and echo prone and harder to tame in general in regards to the room acoustics with most any speaker. In these cases, I think less, ie a smaller speaker like the Micros, can be more.