I chose the 2000 Yamaha V-Star Classic for its classic lines, traditional air-cooled v-twin, drive shaft, and great after market support (after all, I am a mechanic and love to tinker).
I learnt to ride on my mother's (yes, my mom rides) 1997 Suzuki Savage 650, and when the time came to get my bike, I wanted something with a bit more oomph while keeping the cc down to afford to insure the bike (I'm under 25 and a new rider). I wanted something that was great in the twisty country roads, but was still comfy enough on the highway. I wanted a bike that would achieve 250+kms to a tank (I like to go past at least a few gas stations without needing to stop). And lastly, but definitely not least, I wanted a bike that was comfortable to ride and just plain fun.
The V-Star gave me all of those and then some. It has great low end grunt to it and pulls strong through. It has no troubles hitting 150km/hr, although she's definitely screaming anywhere near that. I did not buy my bike for speed, I bought it to cruise the country a little more freely than in my big old pickup.
I find its seat and controls perfect, and very comfy for even a big guy like myself at 6ft 270lbs, but after about 3 hours I'm ready for a coffee stop. The bike is incredibly smooth, and is great in the turns and very stable, and offers a lot of confidence (already hitting the pegs). The appearance is exactly what I was looking for, and I love the red and burgundy two tone paint.
All in all, I'm very pleased with the bike and feel I will keep this one for some time to come (of course with some goodies along the way).