the trail boss is a tiny bit slower the 250ex but it has more pick up. the trail boss is more comforable and has better suspension. the boss is also easyer to ride.

 

Trail Boss all the way here. We had one for 2 years and my wife loved it. I rode it often, then got on a 250ex a couple times. The 330 is much more stable and much more comfortable. The shifter on the 250ex is the worst I've even seen. It's about a 2.5" motion to change gears. It also has a TON of lean around corners. Honda, put some springs on that thing!

The ex is just a touch faster, but the 330 is safer and can go through more stuff. If the lil wife gets on the side of a hill and stops, all she needs to do is hit the gas with the TB and go on up. With the 250 she has to fight with that shifter for however long and try to get back going up that incline without rolling backwards or flipping.