As someone who's owned a few bikes, I'll share my thoughts.
Something like this would be a great beginners bike. It was by far one of the most fun things with wheels I've owned. I will say however, not a great highway bike. Being able to screw around off road a bit was a blast and the thing cornered better than most sport bikes. Very easy to ride, not enough power to really get carried away. They can be had for pretty cheap too. As long as you change the oil regularly they run for a long time too.
Plus you can put knobbies on it and really have a good time.
Not a beginners bike.
This one was a lot of fun, easy to ride but I found that I'm just not comfortable on cruisers in any way. It handled surprisingly well and was pretty quick. I just hate the riding position.
Those 250 sport bikes can be fun, but if I had to do it all over again I'd pick an enduro or supermoto type for my first bike. They're fairly light, maneuverable, easy on gas and insurance, a blast to ride and they're relatively cheap.