@midlifecrisis Bro, I'm 52 and have owned my XR for maybe 3 weeks? 65 miles on sidewalks, roads, and my favorite--a 5 mile lakeside dirt trail with plenty of roots, rocks and such. No prior boarding experience of any type, and such an amazingly good time. It's a great workout for all sorts of muscles just responding to the offroad obstacles you have to maneuver around. I've been sore in plenty of places that aren't accustomed to getting worked. As far as road riding, it's wonderful just to make nice, easy carves as you go down the street.
I've never ridden the Pint, so I can't speak to that. But I appreciate the extra range on the XR and I have no plans to do anything extreme. You won't regret it!