What's wrong with River North?

Development of highrises north of the river started in the 1920's, with the Allerton Hotel, the Wrigley Building, etc, setting the early precedents. And now, 85 years later, I am somewhat confused. Sure, North Michigan Avenue is incredibly dense, and is possibly Chicago's greatest skyscraper canyon. Streeterville is also a sight for sore eyes. But west of, say Wabash, River North descends into a milieu of midrises (many of which should be preserved), ugly ass parking garages, and parking lots. What's going on here? 85 years--yet west of Wabash, little to show for it. Why isn't this part of downtown as dense as the loop? The other part of this question is--despite modern NIMBYism and other factors, will the area north of the river become as dense as the loop some day?>