What I do find interesting is this. (And please, this is PURELY anecdotal so take it with a huge grain of salt.) Webb seems popular among the Virginians I've talked to from military families and traditions. His past service to this country may get those Tidewater-Norfolk-Virginia Beach votes John Kerry couldn't get. Oh, believe me...I know Kerry SHOULD HAVE gotten those votes. But there's a difference in some voters' minds between a decorated hero from Massachusetts...and one who served in the Reagan administration.
Kaine beat Kilgore in Norfolk, Newport News, and Virginia Beach, and he's not even a veteran. There is no doubt in my mind that Webb can do the same. Plus Phil Kellam is running a great campaign in Virginia Beach to unseat Thelma Drake in the 2nd District. This could help bring a lot of support to Webb from this area.
To win the election, Webb must win handily in Northern Virginia (and especially the more conservative exurbs like Loudoun and Prince William Counties). He also must strongly capture metro Richmond and try to make inroads in Hanover County, Chesterfield (always a challenge), and Fredericksburg. If he can win Hampton Roads, as well as take enough votes away from Allen in Southwest and the Piedmont, he can win the election. Of course, that last part is the most challenging, but with Webb's moderate social stances and pro-Second Amendment views (not to mention that he has roots in the panhandle), I believe he will do better in Southwest than most people expect.