Painting sounds like fun and you have some great ideas so far. If you would like a different idea, other than paint, you can use Mr. Potato Head pieces. At target they actually sell Mr Potato head pumpkin packs. My daughter was 10 months her 1st halloween. We bought the Mr. Potato Princess pack. We had to put the pieces in first to make the holes and then let her try. Any potato head pieces will work.