You could use the centroid of the various shapes to test if inside the boundary. Centroid is simple calc for circles obtuse polygons. More difficult for polylines (convert to Region then use vl-get-centroid, or use old school MassProp, or solve by geometry). If your shapes are blocks whose insertion point is at the centroid, then the problem is really simply.
However, will still need to resolve how to handle the condition where a centroid falls exactly on a boundary.