PS, I use a combo satin / moon set (ie, 2 different sets) for more resil. 2x2 set bonus. Crits are my friend, and have the spirit so I don't go OOM. Also open to suggestions on how to gear for disc arena from those in the know!

Allowed to roll?
I've seen this issue come up before, and for some reason it rarely seems to end well. I've seen lootmasters ask all of the appropriate class to link their current PVP piece that would be replaced; but which way do you go from there? Is it more "correct" to give the item to the person for whom it is a bigger upgrade, or the person whose gear shows that they PVP a lot more? Same goes for if you ask how many honorable kills, or link achievements, etc.
My own take is that whatever criteria is customary on your server for determining a player's "right to roll" under normal raiding conditions should be used, and not be further complicated by investigation into PVP "worthiness" or anything similar. It just prevents a lot of headaches.

Should have passed?
Always up to the winner. "Should" is a bad word here; kindness is always appreciated but never to be expected or mandatory. No one should get a bad rap for not passing something if they won the roll, provided it was appropriate for them to roll on the item.

Should have not asked?
Nothing wrong with asking; the worst they can do is say no, right? But I would have offered something for them. Couple hundred gold, some gems/crafting mats, etc. just to make it worth his while. It's his item; trade him something he'll get reasonable value from.
On the other hand I've known of individuals who, in seemingly every single raid, pester someone to whom they lost a roll, under the Anything Goes premise - "if I can convince him to hand them over, through begging, coercion, bribery, intimidation, or anything else- then I win". Nobody likes that guy. Don't be that guy. :)

Well Matt, I think it's the same concept with spec gearing. If you get a piece of loot and one person wants it for the spec their using currently and the other wants to start a new set or for their offspec, the person using the current spec should get the piece appropriate.

You needed it for your current spec, and he needed to start one. You should have gotten that piece over him, regardless of the role.. You needed it right away, not him.

I have decided to be the organizer of voa 25's with a loot system that treats pvp gear as important, as opposed to the way my server tends to treat it 'oh, pvp gear, roll if you have a class'.

This way, frankly, I don't have to convince PvE people that pvp gear shouldn't go to 'whoever'. Well, not the wrathful stuff.

I guess Logan's got a valid point. If they do needs & greeds, and need rolls are restricted to main spec main set (the way our runs usually are), and your main spec/set are PVP (logically you wouldn't be wearing your full PVP set in a raid, but you should still be able to claim it as your primary set), then you would be allowed to roll need on it, and the other guy would only be allowed to roll greed on it.