With the TW at least you can get a sense of community and usually non judgmental support offered here.
No fuel injection, little power & little suspension but lots of commiseration from a cult-like following has it's merits.
If the plan to to ride frequently with friends on bigger bikes then perhaps get bike with similar capabilities to fit in, or just get different friends with TWs.
I've had open class riding buddies where the shared experiences didn't last that long. I would tend to lead them into slow tight woods and they would rather lead me into higher speed more open country routes.
I think the TW can be more versatile and perhaps more forgiving to a new rider. Slow crashes often hurt less than faster get-offs at higher terminal velocities. Have enjoyed several off-road TW group rides with 2-up riders that didn't result in divorces. Slower, lower TWs seem to be succesfully used to combine interests like fishing, hiking, wildlife photography as well as hauling mtn bikes and surfboards.
I'm a 95% off-roader and enjoy exploring with frequent stops to enjoy the outdoors, relax, eat, drink and wave the camera around just as much as the racing around of my youth.]
EDIT: What got me initially interested in the TW over more conventional offerings was seeing a pair of hunters packing big horn rams out of Idaho back country on TWs with what I assumed were Cycleracks. This big load hauling may be hard to replicate in an XT250. In leu of a rack a buddy uses Giant Loop bags on his XT250 and WR250 for multiple day outings.
Here he is in a few cameo shots on the WR with Giant Loop loaded for a 3 day ride some 200 + miles from home. With a TW I would have to haul the bike on freeways but he would ride the XT and WR from home. Something to be said for that.