Being more liberal than Hillary isn't enough to provide a challenge. There were people on the stage in 2008 more liberal than Obama to challenge Hillary. You need a charismatic figure.
Webb is not that man.
Yes. This is correct.
You mean Mike "The Rock" Gravel wasn't a good candidate??? Who the hell are you guys planning to nuke?
DOA. At least when gadflies run in the Republican Party, they can just win favor with one eccentric millionaire and get off the ground that way (Newt Gingrich and Sheldon Adelson; Rick Santorum and Foster Friess). As long as they'll look after their pet/industry interests, the checks will keep coming.
The Democratic Party's equivalent big money donors aren't content to simply have someone who stands for "what's good for my business." They have to have a personal affinity for a candidate and the sort of hedge funders and venture capitalists and Yankee heiresses who make up Big Money on the Left are not going to fall in love with someone like Jim Webb who would probably order a mass-market beer at dinner and make them spend all night listening to him talk about Ulster Scots immigrants in 17th century Virginia.
I listened to Webb talk about the Ulster Scot immigrants on C-SPAN once. It was quite an interesting lecture.