The NYT had a couple of interesting articles this week on art collecting. The first talks about the intimidation factor of buying art and some options that you might want to try. A second article provides an example of someone who's built a collection.
Of course one of the ways the first article suggests dealing with the anxiety involves way more money than you (probably) and I (definitely) have. As an alternative you can get one of my pieces for way less. Value appreciation not guaranteed! ;-)
Green and Blue. Oil pastels on matboard. ~10" x 10"