Most of the reason why the buildings on this commit look so sloppy is I hadn’t used a good overlay. The bing one is simultaneously low resolution and was taken during the summer. The mapbox one is much higher resolution and Maxar Premium was during fall so tree line isn’t obstructed. Kicked myself pretty hard after noticing that. Also didn’t know about the make rectangular tool though.

When doing this change I had looked into whether Dupage offers parcel data and it actually looked like they did. It may not have building layouts but it has addresses. I couldn’t figure out a good way to filter down by location or anything though. It looks like the parcel info references some secondary object for locations and I couldn’t find that.
https://gisdata-dupage.opendata.arcgis.com/

Yes. Got them and the street lights and hydrants while walking my dog. That’s why it’s only on those couple roads.