I would totally shop these two. The OBW would be my choice if I could live without the extra room of the Highlander.
As for the Tribeca Subaru figured out far too late that having the smallest third row, smallest cabin, and smallest cargo space in the segment with some of the highest pricing means slow, or pretty much non-existent sales. They only moved them when they put a LOT of cash on the hood. Honestly, sitting next to the OBW the Tribeca seemed odd. It had the same driveline, drove way more like an SUV, (meaning not nearly as fun) didn't offer much more room, as was thousands more.
Some friends of ours have a Tribeca (2011) and love it. But, they got $10K off, and that made it a good buy.