Well if you have someone who travels down there they can bring back $100 worth of them, which should buy you about 4, maybe 5 of them.
But as for a cigar shop being able to buy boxes of them wholesale and then you buying them commonly at retail, that may take quite a while for that to happen, if ever.
President Obama as the authority to dictate foreign policy but he does not have the authority to alter the embargo, which was not only passed by Congress and signed into law, but was actually strengthened by congress and then again signed into law. Most members of the GOP oppose the actions of the President today and quite a few members of the Democratic party also oppose his actions. It is very unlikely that the next congress will even consider bringing up a repeal of the trade embargo. Now the President can allow some sorts of trade, especially on humanitarian/medical grounds, but I don't think that a box of Cohiba, Monte or RyJ will qualify for humanitarian trade.
So the odds of you buying Cubans legally any time soon? Not so good.