This is pretty near where I live. I-90 Exit 5 is a little strange. The Eastbound exit ramp puts you out right at Calumet and 142nd (not currently a waypoint). The Westbound exit/entrance ramps are from 141st street a bit east of Calumet (with a waypoint at Calumet labeled 141stSt), and the Eastbound entrance ramp is on Calumet a bit north of 141st street (labeled I-90(5)). If, in your travels, you only use the Eastbound exit at this interchange and then travel south on Calumet, you never pass through the two existing waypoints. I guess the most accurate way to fix this would be to add a waypoint called 142ndSt, since I-90(5) is already used.
Side note: For I-90, the Exit 5 waypoint is directly on the Westbound exit ramp and perhaps for best accuracy should be moved halfway between the Eastbound and Westbound ramps.