Originally Posted by
Shippou-sama
My only concern is that Naruto doesn't really work well with others, and would fairly adequately muck up Shikamaru's plans. Also, a flaw for Shikamaru is that he may or may not be willing to actually come up with tactics, since he tends to let others take over, and only acts when he has no other choice. Regardless of teammates, Naruto will always try to take command, thus Shikamaru may not get the chance.
I do see the advantages of having him in the group, with a more useful variety of jutsus. Part of his usefulness comes only from the dreaded "in a tight spot" (frog boss). This is another thing to try and avoid, as it massively unbalances any characters performance. Remember, we want to find a team to handle all their missions well, which includes everything in the range of picking trash out of a river to eliminating an enemy from another village.
And, as I've said, my team is far from perfect, I realize. =P