I'm not saying it's the way to go. As I pointed out, being experienced and being good went hand-in-hand for the founding fathers. And, some inexperienced presidents didn't pan out as with Grant and Harding (who weren't personally bad but put together the worst Cabinets you could imagine and let them run amok with other criminals and dipshits).
Sometimes it works, sometimes it doesn't.
For reasons already stated repeatedly, I definitly think Obama can end up in the field of Teddy Roosevelt and JFK.
In Hillary's case you start with her experience, which is dubious as it is. From there you have her two biggest moments for personal impact: her biggest domestic issue was health care as First Lady and that panned out terribly; as a Senator overseeing foreign policy she neglected to look into the subject and voted for a war in Iraq. Two key issues/events, two huge failures.
Hillary, with all her "experience", has displayed the same judgement and ability to get the big shit right as Lyndon Johnson and Richard Nixon.