Cigars are like beers - lots of different flavors and only you can decide what's "good". Everyone's palate is different.
I've learned I favor Nicaraguan habanos and corojos (or a mix of the two). The few maduros I've had don't appeal to me, and I don't have an interest in Connecticuts and mild flavored sticks. The one I keep coming back to is the Perdomo Habano Corojo. Part of it is the name, but the other part is knowing which leaves are used. As far as flavor, Cigars International (and other sites) is pretty good about labeling the strength, and you can start at a pulldown menu and select the strength you want.
I by no means am heavy into cigars. I get by with a 5-stick travel humidor (the black plastic ones) and the replaceable pillow. I'll either order a 5-pack from CI or grab some locally from a store. CI usually has deals that include a humidor, a cutter and butane lighter. Though, there's something very pleasurable from properly lighting a cigar from the heat of a lit match (not from direct flame contact with the stick).