Best starter bike cruiser for the money?

I believe Yamaha made a Virago that size and they're decent bikes. Honda has a Rebel 250 that the police use in DC and they work very well. Most states offer a special motorcycle training course which I have heard is the best way to learn if he's never ridden before.

It depends on how big your son is. Short riders often have no trouble on the Honda Rebel or Yamaha Virago. If he's 6'2", the only 250 cc cruiser I've seen that could be comfortable at that height is the Hyosung GV250, also sold under the United Motors name.

Take a look at the Suzuki S40 (older models are called the Savage). It's a 650 single cylinder bike he won't outgrow or be sick of after a month.

It comes with forward controls and also has belt drive which makes maintainence a piece of cake.

It's also fairly low to the ground and not very heavy. There's also only one carb so you don't have to worry about keeping multiple carbs synchronized.

Honda Rebel or Kawasaki Vulcan.