I first simplified the contours a bit to be able to drape at all (even from contours seemed to stall). Then closed the open ends of the parking lot and draped the road which indeed did not seem to fully drape so turned on hidden geometry to try to identify the problem.
I painted the facets one by one until found out that in one of the handicapped parking lots) in the corner) there was some problem. Redrawing the edge from the corner point seemed to solve the issue.