I think a significant problem that Obama has, which will come to
light, is a personal characteristic of his seeking to to avoid
difficult choices and take an EASIER way out of a situation.

Here are just five examples. 

(1).  As a child and young man, he was called Barry, not Barack.
That was EASIER for him and for the people who knew him. 

(2).  In 1988, at the age of 27, he became a Christian to enable
a career in politics and to enable a relationship with Michelle
Robinson, who later became his wife and the mother of his
children.  It would be a lot EASIER to be Christian for politics
and for dating.  To read a fact-based, fictional satire called
"When Barack and Michelle First Met", go to this link:
When Barack and Michelle First Met

(3). At the Harvard Law School, from 1988-1991, he was known as a facilitator of compromise between
opposing  advocates.  He promoted his personal attitude of taking
an EASIER way out.  In my view, it may be hard to compromise
sometimes, but it is a lot EASIER to have opponents compromise
than to have one side successfully advocate and win the
opposition over to its side.  A related article, "BARACK OBAMA: A MEDIATOR OR A LEADER?" can be read at:
BARACK OBAMA: A MEDIATOR OR A LEADER?

(4). In the often-mentioned October 2, 2002 speech in which Obama
spoke out against the U. S. going to war in Iraq, Obama, an
Illinois state senator, stated,        
     "What's tempting is to take the path of least resistance and
keep quiet on the issue, knowing that maybe in two or three or
six months, at least the fighting will be over and you can see
how it plays itself out." 
Here is a link to this speech:
Obama's Iraq War Speech

In my opinion, the temptation to "take the path of least
resistance" is a  temptation to take an EASIER way out, which
apparently he had yielded to before the speech and after the speech. 

(5).  In 2003, rather than Obama making a difficult choice among
(a) confronting and challenging Rev. Wright about his hate
America rhetoric or (b) leaving Rev. Wright's church, Obama took
an EASIER way -- doing nothing. 

Finally, in my opinion, Obama's personal characteristic of
seeking to take an EASIER way out of making difficult choices
will be a big negative with respect to his electability.  To me,
this is not a characteristic of a good leader.