The sad reality is that we do not even know whether Obama's "personality" is a real thing or not thanks to the love fest of the MSM. And even though he IS someone the MSM claims to be, I do not think independent voters would find Obama is more "likable" than McCain who is, actually, very likable in many ways (and his good personality has a very solid one which survived all the terrible scrutinies). Destroying McCain using Obama's irresistible personality??? Not only unrealistic but also a terrible miscalculation.

One thing I've noticed over the years is that the Democrats are always really really clumsy when it comes to character attacks.

If the strategy is to paint McCain as unstable, for example, they won't just go out and subtly build the narrative.  Instead, the first step will be an anonymous quote from a campaign strategist in the NYT that says, "We're going to try and paint McCain as unstable."

I honestly have no faith in the Democrats to ever get this right.

I think I agree with you to an extent, and I think the specific strategy chosen should depend on who our nominee is. I don't think we really have to "personally destroy" him, though. McCain has a lot of good will, and if our campaign to destroy his character is too agressive, it could backfire. Some character attacks are cleaner (i.e., more dignified) than others, and some care should be taken in designing these attacks. I would first go after his straight-talk reputation, which shouldn't be too difficult. Matt Yglesias has had a few posts recently highlighting McCain's flip-flops and inconsistent rhetoric (on global warming and immigration, for instance). Similarly, McCain's recent pandering showcases how illusory his straight-talk reputation is.

Also, I would highlight McCain's incompetence on policy issues. Specifically, he has demonstrated a surprising inability to discuss economic and educational policy in any kind of comforting detail.

Finally, as Romney's campaign has tried to highlight, McCain has a rich history of interpersonal squabbles and outbursts. Bringing attention to this reduces his likeability. In relation to McCain's likeability, the CNN focus group last night reacted quite negatively to McCain when he was being hard on Romney. The more we can show this side of McCain the better.

As it relates to dirty money and stuff like that, I think Obama will be in a much better position to deliver that kind of criticism. Also, I think Obama will be in a better position to criticize McCain's enthusiasm for continued presence in Iraq. He also makes McCain seem even more ancient.

true, but i am a nobody- so i am not worried they would  care what i think.

I think you have got the main point exactly right.  There are a couple of nuances though.  There is a difference to me between personality and character.  Personality is more superficial and falls along the lines of who you want to have a beer with.  The later involves understanding more about a person's development, background and family dynamics.  See the recent NPR Fresh Air interview of Jacob Weisberg on some of this (start around 17:00).

Like another other demographic, conservatives and independents are not monolithic and each individual of the demographic doesn't follow the rules you describe.  For example I think there is a subgroup of independents that are so progressive that for them the difference on some important issues between Dems and Repubs become insignificant.  The example uppermost in my mind is the high level of support the Dems gave Bush in the AUMF.

I've seen evangelical neighbors get really excited about Obama.  His openness to people of faith, even evangelicals, is getting him support.  They sense that even though his positions are 180 degrees different sometimes, his values are from the same foundation.  Now part of this alarms me and I have held the view that many evangelicals are extraordinarily naive.  They are willing to support blindly someone who talks the Christian talk (like Huckabee) but doesn't walk the walk (Huckabee's confederate flag pandering).  I find that the evangelicals I know are at least more aware of having been manipulated by Bush and are a little less naive.

Listen (don't read) Sen. Obama's speech at Ebenezer Church for an example of what I'm talking about, the "empathy deficit".  It's one of his best and if you have the time to listen to all of it you may find that he echoes some of the same themes as Edwards in some powerful ways.

So I think that not only must the character of McCain be heavily critiqued, but building up the character of the Dem nominee is also important - whoever the nominee may be.

You can't go after his character!  The guy was a POW, for goodness sake, and he's an old man. It will backfire.

To win, we must make sure Americans know what their options are and stress that.  Do they want to stay in Iraq and do they want to get out?  Do they want to go back to the Clinton Economy or do they want to stay in the Bush one?  Those are the choices and they have to be made clear- to win, we have to do it on policy- there are clear differences.  That Americans aren't voting for McCain or Clinton or Obama- but the way forward- they are just the figureheads of the choices- I think that is the way to go.