Seeking Advice: B&W P5 (Series 2), KEF 500, V-Moda XS, or ______________ [I've included details of my usage, preferences, etc.]

A(nother) long-tme lurker seeking Headphone advice. Thanks in advance for your patience and any help/advice. I've already dug through many, many threads here and that's helped me narrow my target to three models within my budget that seem to balance my needs/wants. Below, I've broken things down best I could based on (and within the limits of) my knowledge. Apologies if I've erred on the side of too much.

Basics

• Budget: $200-$300 MSRP, with an eye out for deals
• Preference: On-Ear (compromise for portability; not interested in IEM).
• Seeking reasonably neutral/transparent sound.
• These days, mic/remote is near necessity for me (play/pause is key, volume not so much)
• Aesthetics aren't too important, but prefer minimalism.

General Use:

• 90-150 minutes of daily outdoor walking (mostly paved paths where closed headphones seem to thump with every footstep)
• iPhone 6 (ALAC files transscoded to AAC 256, podcasts, audiobooks)
• Never at home (I prefer my mid/hi-fi setup)
• I'm not too concerned about isolation but am very concerned about leakage
• Note: have had persistent ringing in ears since childhood

Personal sonic preferences/priorities (take with a grain of salt since I don't expect all these qualities within my budget; these are based on head-fi's glossary).
Articulate/detailed, balanced, airy/breathy/spacious presence, transparent.

Current Contenders (based on reading):

1. Bowers & Wilkins P5 (Series 2)
2. KEF M500 (these seem to be a step up sonically from P5)
3. V Moda XS (especially if these have better midrange than the 80s I sampled)

What I've sampled in-store:

1. B&W P5 (original): Overall favorite from my limited sample; detailed enough I could pick out some buried details in songs; decent bass without overwhelming the midrange, enough treble to not feel distractingly muffled or bright.
3. Sennheiser Momentums (really liked the look and feel but the midrange was so lacking that even Johnny Cash was buried in his own mix).
5. V-Moda 80 (these felt comparable to the P5 to my ears; they had better punch on kick drums but were weaker on vocals).
7. Grado 80 & 125 (*loved* the airiness but the sound leakage was so intense they're out of contention).

Snapshot of Music Taste:
Frequently:

• Coarse, deep singers (Leonard Cohen, Bob Dylan, John Prine, Tom Waits, Johnny Cash)
• Alternative and Rock (R.E.M., Wilco, Travis, Beatles [occasionally random classic rock, Pink Floyd, etc.])
• A wide variety of acoustic singer-songwriters (even mix of female/male)
• Jazz (Gene Krupa, Art Tatum, Oscar Peterson, Bill Evans, Louis Armstrong)
• Some soundtracks (John Williams, Jerry Goldsmith, Alexander Desplait)

Less Freqently:

• Massive Attack, St. Germain, Paul Oakenfold
• The Who, Led Zeppelin
• Fugazi, Ramones, Me First & The Gimme Gimmes and other various punk

Based on your comments you made above, I'd recommend the Keff or the XS over the P5 S2. They seem more likely to fit your signature preferences. Good luck on your search I am going to be slightly more biased towards the XS as I've had more time with them, but they both favor well on Head-Fi, I don't think you'll go wrong either way.

Thanks! Any of them would be better than the mudfest Sony pair I have now.

Just ordered the V-Moda XS and they should be here same day as the KEFs.