We test drove the 500 when we were shopping UTVs. We hated the 500's transmission. It's very jerky, with a big pause at each shift. It might be more acceptable in manual mode when you'd know the next shift is coming but my wife would be driving it in automatic so that's what we tried. Our use is 100% utility around the property and private road. If you're also driving on trails in a more sporting manner the 500's trans might be more acceptable.
We ended up with a 700, which has a much smoother transmission than the 500 or the Deere that we tested. The dump bed is very useful.