The chocolate should be smooth and shiny. If there are white blemishes on it (known as bloom), it could be a sign that the chocolate was not properly stored. It could be that the chocolate was warmed to the point where it melted or it was stored in a moist refrigerator. A little bit of bloom shouldn't affect taste much but the texture won't be as smooth. If you're paying for good quality chocolate, you should make sure that it's being treated right.
The main ingredient in chocolate is derived from the cacao bean. A lot of the time you'll see a percentage sign on the chocolate package that tells you how much cacao is in the chocolate. The higher the percentage, the more bitter the chocolate will be. Darker chocolates usually have a higher cacao percentage.
but to taste the complex flavors of good chocolate, I would aim for above 60% cacao. This level is often called semi-sweet.
Chocolates that are above 80% are pretty bitter and not as accessible to casual chocolate lovers.
Take a bite of the chocolate, and let it slowly melt on your tongue. The texture should be perfectly smooth with no hint of graininess. The flavor should last long on the tongue and be pleasant all the way down. This long "hangtime" allows you to search for other secondary tastes. Is it nutty? Is it fruity? Is it woody? Tasting great chocolate is similar to wine tasting in a way.
With cheaper chocolates, I find that that their lower cocoa butter content makes for a less smooth texture and a shorter lasting flavor. Worse, preservatives often lend an unpleasant aftertaste.
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