This discussion comes up twice a year...and I still enjoy it every time.
Neo, I like your Massillon throwback idea but black is just not possible because of the Bengals and Paul Brown connection.
Of everything in this thread, I like the Madden pic KoK posted with the old-school white helmet and B logo best. I don't love the B logo but it actually works decently on white. I've long said that the first thing I'd do if I owned the Browns is develop a REAL logo that represents the Browns and Cleveland and this mock up shows a logo could work on the helmet.
But I think the only way to truly start fresh is to retire the orange helmet from full-time usage and make it our official throwback look. So I'd go with a revamped logo on a white helmet to give props to the original helmet (white) but give us a new identity.
I would then make brown the primary color with white the opposite and orange the highlight -- something like what the Bears do. So brown top, white pants, white top, brown pants. And I'd keep the white/white/orange helmet as official throwback twice a year for special games.
Actually, the Bears provide a really good template for the Browns in that they have made minor modifications but retain a classic look that they shake up with the orange jersey (which I detest, but at least they shake it up a bit). I think the Browns could do something similar by making the helmet the major change and the rest be a minor but very distinct change -- like making the brown stand out more, use updated font, use more orange for highlighting, etc.
Finally, I'd also retire the dawg completely and use the elf as the throwback icon. Yes, he's a bit...flighty...for our 21st century sensibilities but it has a certain timelessness because it's so random and obviously old-school. Makes it the perfect "you're cool if you get this" logo.