I have a board where several connectors need to overhang past the edge
of the board. I'm having a hard time making this happen though because
PCB doesn't like for the silkscreen outlines of these parts to extend
beyond the boundary of the layout. What's the right way to deal with
this situation?
Make the workspace size bigger than the final board. Draw a 10 mil
rectangle on any layer named "outline" (change an unused one if
needed) that's the size of your final board. Now you can position
connectors relative to the outline. PCB will use the "outline" layer
to produce the gerber FAB drawings, and knows how to add that to every
PS output page if needed.