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The Senheiser HD555, by contrast, truly envelops my ears, and as such is the only one out of these three that I would rightfully call circumaural, even though it's the same size class.

I stand by my distinction, which makes a real difference in terms of comfort (IMO), and I agree with your own classification. I'm going to amend the OP about the size, though.
Personally, I can't stand any on-ear headphones, no matter how good they sound: my ears inevitably get sore after a short while.

One common type of portable head phone I'm not sure how to categorize.  The transducer unit is essentially an ear bud, but they have a head band (so don't fall out as easily)  http://www.amazon.com/Sony-Lightweight-MDR.../dp/B00005N6KG/

I mostly use headphones IEMs, as much of my relatively small amount of listening (sadface) nowadays is done whilst on the move or at the gym.

When inside, I use studio monitor speakers, which I assume would be filed under “Desktop speakers”: I use 2× M-Audio BX5a, to which I connect either my iPod (another sadface), computer, or POD X3 Live (guitar/studio multi-effects pedal and USB audio interface) depending on context.

One common type of portable head phone I'm not sure how to categorize.  The transducer unit is essentially an ear bud, but they have a head band (so don't fall out as easily)

When inside, I use studio monitor speakers, which I assume would be filed under “Desktop speakers”

Yes to both, I would classify them as earbuds and desktop speakers, respectively.

So far looks like a pretty low percentage use car speakers.  I wonder if that reflects urbanites and others who don't drive much, or more not using car stereos when they do drive.

I do a fair amount of listening while in my car, roughly an hour a day. I have a full aftermarket setup I'd classify as mid-grade. Definitely all respectable gear, but not what I would call true hi-fi.
I have two, 3-way Kenwood door speakers with 6.5 inch woofers. Two 4-way Kenwood rear speakers (6x9). Also, two Kenwood 12 inch woofers in the trunk powered by a mono block 1200 watt amp.
A fairly cheap Sony head unit ties it all together.
It's a loud, clean sounding system. I have sound deadening material covering the whole inside of the trunk and in other important areas. It's good but I'm working on setting up a home system for flac files and vinyl.
I have a Yamaha Reciever but I don't have the cash for a set of good speakers yet.

I had my eye on these though. Anyone have thoughts on these speakers? yay, nay?

I use virtually every type of speaker on the list at various times, so I stuck the the most often used items..

My living room stereo is driven by a Pioneer VSX-1122-K receiver which drives 2 KLH 3 way floor speakers, each with a 12" woofer, 5" mid, and tweeter.
Media is fed to that unit over the network since the Pioneer is network ready and can play FLAC and Ogg Vorbis natively. I also feed audio to it via HDMI from XBMC running on a Raspberry Pi.

My other standard speakers are on my main computer. I connect from the computer via S/PDIF to a Yamaha receiver (model escapes me atm) which drives 2 Sony 3 way "bookshelf" speakers, each with a 8" woofer, 4" mid, and tweeter. (those little Sony speakers THUMP)

I listen to a mix of talk radio and mp3's in my truck so the car speakers come into play there.

When I don't want to annoy my family I listen on Sennheiser HD-202 and HD-280 headphones. The HD-202 are supposedly supra-aural but they enclose my ears so I counted them as circumaural. The HD-280's are truely circumaural. The choice of which usually comes down to which pair is in reach at the time.

I stand by my distinction, which makes a real difference in terms of comfort (IMO), and I agree with your own classification. I'm going to amend the OP about the size, though.

Thanks, that's what I was talking about. I initially thought that by on-ear you exclusively meant light-weight class phones like these and these, hence my objection.

I don't see a category "Galactic Princess"

Sennheiser cx300 series II iems. Huge improvement over series i. Durable, capable of prodigious bottom end if eqd. Dont break the bank.

I've used Westone IEMs for maybe 10 years now. Usually with foam tips, lately Comply. You can tell when the seal goes or the foam starts to loosen as well. I did once get some custom tips but they make them from solid vinyl which while usually comfortable, means that any change to your ear shape, i.e. caused by regular use of earplugs makes it really difficult to get them to seal. So I went back to Comply tips

At home I use some 20 year old KEF speakers, never for critical listening (what is that anyway?) as the road I live on is too noisy for that usually.

I would say it's when you're doing nothing but listening to music. Not playing music while you're having a party, or listening while you're eating dinner or listening while you're cleaning the bathroom. All of which I'd call background music. I'd also venture that few people today do anything other than listen to background music.

That's what I'd figured. I used to do it when I lived somewhere quieter so it's really just background music these days. I listen more critically on my way to work than at home now!

Plenty of high end speakers take measures to have a wide horizontal pattern while constraining the vertical pattern.

So? Plenty of "high end" speakers recommend using bi-wiring, even though it is completely without merit or evidence that it has any audible consequence beyond the fact that the effective, overall thicker gauge of wire used across the room [double the number of strands of a traditional, single run] alters the L, C, and R of the wire [which in some circumstances may have consequences if the single run is, for example, too thin], but that can be easily duplicated simply by using a thicker single wire pair to a single set of speaker binging posts, from the get go. [Not to say that controlled directivity is "inaudible", and I agree in some instances is quite desirable.]

If one prioritizes a specific directivity pattern over a smooth, flat frequency response free of peaks and dips [not me], I'm sure there are any number of manipulations which can be applied. I agree with the author's AES paper which points out that MTM designs have response errors which are "not predicted by a simple lobing error analysis" that most speaker designers utilize.