RE:
1) Exactly, not being a "regular" hero makes him an odd choice right out of the gate. He's Jonah Hex on 'roids and lacks even the respect for local law that the Punisher has. He's never struck me as heroic at all in 99% of stories I've read about him...so why is he being considered so strongly for a solo film? What role would he serve in a greater cohesive DCU movie universe?
2) It wouldn't, just seeing as how of late Marvel has shown you don't have to drastically alter a character to make him work in a new medium would seem a shame for it to be done. I mean, it even seems the new Dredd film has learned from the Stallone "in name" only film in one regards by keeping the helmet on. At least based on the replies in that grading thread to date.