Yeah it's a strange discount system as it is totally based on the raw count of items, disregarding what they cost to send. As I get closer to that 1000 limit I will definitely get more and more motivated to bridge that final gap by any means.
Now a shipment usually costs me around $3 to mail. At that 1000 threshold the discount will suddenly go from $0 to $300. Sending an empty envelope would cost about $1.