I have the HD25-1, the ESW9A, and the W4, so I might be of some help to you. First of all, even though I have all of these headphones, I don't listen to the ESW9A and the HD25-1 anymore. I find that the Westones suit me for all types of music and I don't feel the want or need to listen to the headphones. Is the sound quality of the Westones better than the HD25-1/ESW9A? Kinda. I personally think that the W4 excel at more categories than those two headphones and that's why I use it. That's not to say that the headphones are worse; it's just that I prefer the W4 for everyday use. The only times I use the headphones are when my ears hurt from wearing the IEMs too long (5+ hrs in one sitting), then I would switch to my ESW9A.
Portability wise, I would only recommend the W4 and the HD25-1. As you may already know, the HD25 is built like a tank. The ESW9 is not. When I am wearing it out, I'm so paranoid with it. Every time my jacket zipper accidentally swipes it, I have a heart attack. Every time I put it down, I have a heart attack. Every time people on the bus swipe my headphones with their arms, I have a heart attack. It's just not good to bring it out because it will just ruin the wood in the long run. You can be careful but you can't control what will happen in the world. Plus the sweat that goes onto the leather, is also not good. It has very to little isolation and there's just no point listening to that over something else. If you plan to frequent very quiet places and don't have to worry about the people and the elements, then the ESW9 would be feasible, but other than that, it just isn't worth it.
I'm looking at your list for what you listen to and you state that you don't listen to a lot of music with vocals, which is another negative point against the ESW9A for you. I bought my pair solely to listen to female vocals, and nothing else. If you're going the headphone route, the HD25 isn't a bad choice for the music you have listed. I have some of the music you have listed and it sounds just fine through the HD25. It sounds better through the W4 though.
IEMs are nice for portable use because of the small form factor and the isolation. But if you get IEMs, you have to be pretty careful with them. The cable is usually what I'm worried about the most. Also, hygiene is a big factor with IEMs. There are many times where I've gotten some ear infections because I wear them outside and stuff just gets on it. I carry small alcohol wipes with me which fixed the problem. Isolation is good, but some people can't stand having tips in their ears for a long period of time, or at all. With IEMs, you don't really need to worry about an amp. I rather not have one so that I can retain max portability, but whatever floats your boat.
I would give you sound impressions but I am horrible at describing music. I personally would choose the W4 among your choices. Hope this helps a bit.