The Harley debate rages on every motorcycle forum. I always thought the "If I have to explain it you wouldn't understand" was a bunch of bullshit spewed by owners who can't think of anything else to justify their purchase. But in the last few years I've changed my mind. The previous post explains it well. Bikes can be emotional purchases and as such a person shouldn't have to explain.
I have a hard time understanding why a lover of the cruiser wouldn't get a Triumph Rocket 3. Same price as a Harley. 2200cc monster that produces 150ft/lb of torque (HD - 92) and 140 hp (hd - 75). The motor is engineered to be placed low in the center of gravity of the bike. The local dealership insists that people sit on them to demonstrate how light they feel. They have a shaft drive.
But all that doesn't mean shit if you don't like the way it looks or feels when you ride it.
Anyone looking to get started riding I suggest the single cylinder Kawasaki KLR 650. They take a beating and can be found cheap. I bought this one with 50,000 miles for just over $2000 and rode it to Alaska. Here it is on the Alaska Highway.
I sold it to an Australian for just under what I paid for it. I get an email every so often from the owner. Here it is years later in Columbia.
I'm selling my current bikes because it is too pretty. I want something I can take anywhere and not worry about.