I think a proposition like the OP suggested wouldn't go anywhere. Too many hot-button issues all packed in one. HOWEVER, an initiative for a constitutional amendment, or a law requiring shall-issue to qualified persons, might. I see the pessimistic (realistic?) side of things - the money, the time, the fact that CA recently had such a proposition and it couldn't make it. The NRA might not back it. GOA might help, I don't know. (I'd hate for it to become a fight between the NRA & GOA, causing infighting and a whole slippery slope. *shudders*) Hold a bake sale or 20,000...I don't know!
Tips? If you go for it, definitely go for the "core" groups - ranges, gun stores, etc. BUT, there are plenty of people out there who don't even own firearms and support CCW. Or who
would, if it were explained to them. I know several who I think would happily sign. Try
colleges, particularly after VT. Get young(er) people to mention it in their blogs (and MySpace/Facebook, too). Coordinate with groups like the College Republicans. And don't discount the third parties - Constitution and Libertarian! Their people might be far more active and ready to volunteer than Republicans.
I'm rambling I guess, but the possibility is out there. In the meantime, let's do our best to "come out of the closet" when possible, to show everyone that gun owners & those who support them aren't the boogeyman. Many people tend to vote with their emotions as much as their heads, and knowing that "Well, So-and-So shoots/supports CCW, and he/she's a really nice person..." does a lot to sway opinions in your favor. Of course, this might be the best way to go about effecting change period. One person, one business policy, one college regulation, one state at a time...