If I had to choose b/w the TW and the CRF250L, and they were within a few hundred dollars in price, I would go with the crf. However, the reason many choose the TW is because it is low to the ground and unique looking. TWs are interesting looking bikes and have good manners on/off road. The TW is non-intimidating even for new riders. The CRF (I haven't looked up the seat height) will be taller, faster and have more power. All of these are great things for more experienced riders but mean nothing to a new rider. The TW is not pretentious and does just what it was designed to do. It has its limitations and its strengths and has to be ridden with those in mind. I like the feel of dirt bikes because I grew up riding MX bikes and trail bikes. The TW is a different style of bike than what I'm used to but it is fun in its own way. It's more mellow and laid back.
I like them both but if they were offered to me I would pick the Honda just because I like to rip around the trails and enjoy the taller stance both on and off road.