He will definitely be criticized by the right/GOP. He will likely be criticized by members of his own party.

However, I do not think anyone should be surprised. When he campaigned he said that he would talk to world leaders without preconditions, he was hammered by Clinton for saying this. Granted he later modified his stance a bit, but he seems, in general, to be going forward with what he said that he would do.
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It never hurts to be friendly. It doesn't mean that you agree or approve of the views of the other guy. Our whole situation with Cuba might have worked out differently if we had just acted a little friendlier in the early days. Same with Nicaragua. Castro is not one of the good guys, but he was never Hitler.
Younger leaders who are enamored of a particular ideology like socialism need time to experiment and learn the limitations of their ideology. Not commenting on their efforts is often the best policy for another country. In international affairs, silence is often golden.
Older leaders should try to remember that younger people don't have the insights that age brings. They need to be patient and listen, because just allowing younger leaders the freedom to discuss their ideas will often cause them to modify those ideas..
Even when we firmly disagree with a country, it does not hurt to face them with a smile. There will always be plenty of time to frown.
Let South America do it's thing. They are not a threat to us. If their economic efforts lead them to disaster that will not damage our economy.
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People will realize he shook his hand, and the world hasn't come crashing to it's end!

It's the year 2009, the USSR doesn't exist, and America has hundreds of threats greater than little old Cuba, sitting their by itself.

Time to move on and focus on something important...like the economy, global warming, or actual threats like Iran
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The tricky thing about Cuba is that Castro is a repressive and brutal dictator. But his argument is that he has to be omnipotent and root out dissent because of the American blockade that has literally cut off his country from imports and has lead to a lot of the poverty that has stricken the island. Granted, if they didn't have a brutal dictator, things would be a lot better.

As a result, you sort of get into this chicken/egg argument over where the blame lies. The left can argue that a lot of Cuba's problems are caused by the American blockade, and this has empowered Castro. The right would argue that because of an empowered Castro, we need to have a blockade. No one is really right, but it doesn't solve much. We'll see what happens when his brother Raul takes full control after Fidel's death.

Churchill used to say, "Democracy is the worst form of government. Except for all the others."
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