His immigration position being a "concern" is a bit of an understatement, considering how dependent among Latinos the Democratic coalition has become.
Not if they can win back the white working class.
Yeah, and the GOP would have a permanent majority if they could win back blacks.
Webb can win back whites.
For the GOP to win back blacks, the generation of blacks that were activists at the time of the Civil Rights Act would have to die out first.
Based on what? Obama outperformed Webb in Virginia twice.
Just because you're a white Southern male doesn't make you suddenly appeal to working class whites (see: Gore, Al).
Obama wasn't running against an incumbent Senator and a heavily entrenched Virginia politico. Taking results out of context like that is pretty terrible analysis and I'm sure you know better.