I have always believed that the spring pin has two functions: it is used both to centre the cutter on a punch mark and then to eject the slug from the cutter once the hole is drilled.
Using the cutter in a milling machine, without the pin, it is always a pain to remove that slug.
Individual cups would not be required. A single one with a conical internal recess would work for a range of cutters, a smaller cutter just bottoming out deeper into the cup. Think about how you drill a hole with (say) a #3 centre drill. Following that with a 3mm twist drill will touch the conical recess deeper than following it with an 6mm twist drill.