^Perhaps. Believe it or not I do have a little bit of a soft spot for the Stallone film and yes they did try but as you say it was being pulled in too many directions at once. As for the character himself, for me the main issue had nothing to do with the helmet (though it certainly didn't help) it was what I sometimes refer to as the "John Wayne Effect." By that I mean that for the most part, no matter what film Wayne was in or what role he was supposed to be playing, he was always playing John Wayne. Just so with Stallone (and a few others I could mention.) His persona was such that (with a few notable exceptions) you could never get away from it. He wasn't playing Judge Dredd, he was playing Stallone dressed up as Dredd.
Still like I said all the fretting is moot since it's been confirmed that Urban won't take the helmet off, at all.
As for the 3D, as I said on the previous page I think it'd be worth it in this case.