SketchUp Shop Challenges - What am I doing wrong?

It’s not a bug. The thing you are butting heads with here is when you get too many segments in a small arc or circle, the points effectively merge due to the tolerances set in the software. The reason for telling you that you’ve chosen too many sides for the arcs/circles is to prevent you from creating models that can’t be printed because they aren’t watertight. The easy solution to this is to work in meters instead of millimeters. You enter all of your dimensions as if they are milleters but units are set to Meters. STL files are unitless so it really makes no difference that the units are set to meters. Tell the slicer software that the units are millimeters when you import the STL file.

Additionally, you may not need as many sides in arcs and circles as you are setting. Depending on the printer and the application, you might be able to get by with fewer sides.

This solves your issue in #4 as well.

Show an example. Is it because you are working at such a tiny size and maxing out the number of segments? If so, my solution above will sort that out.

Here’s a quick example. The model was created using meters as the units.

I exported the STL from SketchUp, uploaded it to i.Materialise telling them the units are millimeters. No need to scale the model down before exporting.