On the pro side, Obama taking his family vacation in the Gulf would demonstrate the appeal of the area and thus, serve as endorsement for the idea.
On the con side, with everything going on in the Gulf at this time, security for the first family might be an issue. More than that, why would ANYONE want to take their family on a vacation to an area where they would be likely to have to engage in work?
This appears to be an opportunity for Obama to "sell" the Gulf by taking his family there. It is also an opportunity for him to spend some quality time and relax.