Barack Obama and alienated Democrats

This line of attack is weak. 

Point 1 is a simple ideological tag line.  Yes, this has power in the electorate, and McCain is viewed as different enough from other Republicans that he can probably use it somewhat effectively to rally some usually Republican independent voters, but the terrible environment is going to take away a lot of the power of these generic party tag lines for the Republicans this cycle.

Point 2 will only resonate in the conservative blogosphere, on Fox, and with Limbaugh, where the audiences wouldn't vote for Obama or Clinton.  Really, does McCain want to go to undecided voters stacking up his list of past ethical problems, lies, and the long list of old guard K-Street project beneficiary Republican lobbyists he employs against... what equivalent from Obama?  My obvious political leanins aside, the man just hasn't been in public life long enough to put together a bad list in this category a tenth as long as McCain's, regardless of whom you would prefer as president.

Point 3 is the only opening here.  I personally think the tide swings so hard against the Republicans this cycle, and people really do want something different enough from the past so as not to be strongly drawn to a 72 year old Washington insider, that it won't.  But there's definite possibility for play with this one.

Point 4 again is just a standard party tag line.  Readers here will read into it all the things they don't like about Democratic policy preferences, but Republicans have heeded to a much more Parliamentary style strict ideological line and with much greater discipline than the Democrats have, and the pushback this cycle again is not going to give this any play outside the party base echo chambers.

This isn't to say there aren't many equivalent party lines and echo chambers and all on the other side.  It's just that the current conservative run's crapped out...