I’ve said it before in other posts and that is that I believe the Kawasaki Vulcan 500 to be the best entry level cruiser on the market. Considering your friend’s size it should be right up his alley. Despite the smaller engine it is actually more powerful than the Honda Shadow VLX 600 and is nearly on par with the V-Star 650. Of course the fact that it’s engine was originally designed for a sportbike (the Ninja 500R) is mainly responsible for that.
The V-Star 650 is another good choice worth considering but I would stay away from the Honda VLX 600 as many riders have described its lack of power output as “scary.” Its engine only puts out 35 horsepower, which is less than that of a Buell Blast and only 10 more than that of a Kawasaki Ninja 250R, but it weighs considerably more and isn’t geared properly to be able to take advantage of what power it does have. My dad, who rides primarily smaller bikes such as his Kawasaki KZ400, took one out for a test ride because he was considering buying it and said that it was just scary because despite being a 600 it didn’t have the power to be able to accelerate its way out of emergencies or turn left at an intersection with no left turn signal in between cars.
If you’re in the market for a used bike, Yamaha used to make an entry-level cruiser called the Virago 535 that was replaced in 2001 by the V-Star 650. It was an air-cooled V-twin with shaft drive, so there was practically no maintenance needed at all.