In terms of making a game with them, I think a design where the pins are on the face of the card may be useful. I want to be able to 'draw' a card without knowing what is on it.
Certainly can be useful with pins on the back (and I totally get how this orientation is probably more size-efficient), but I think front pins would be more 'playable'. Maybe a design could be achieved with holes that pass through all the way so it can be written with either orientation?
Being able to 'power up' an existing card in the upwards orientation could be really cool for situations where you kind of want 'counters' applied to a portable card. Could have a base-station that allows you to 'add' the qualities of one card to another target card, or 'evolve' a pokemon, etc.