Thanks!
Properly jetted and geared, 2 strokes are fine on the road. I've ridden my supermoto all over the place with the only ill effects being numb hands from the vibes at certain speeds.
With riding spots 45min to an hour away though, I personally wouldn't even ride a 4 stroke dual sport to the trails. It would be trailered. That's a bit far to go without a support vehicle should something to wrong with the bike (or more importantly, the rider) given the knarly single track we ride most of the time. I'm lucky enough to have a couple great riding areas within a 15 minute ride which is ideal for a plated dirt bike. Don't want to wear down the knobbies too quickly if I don't have to.
In fact, I just got back from a quick ride through the trails. Gotta get me a GoPro camera so I can post some vids.