That $1000/kg figure is reprocessing something like 10kg of material to get 1kg of enriched material.
Current costs to launch a kg to orbit are something like $2,000-$6,000.
If we're comparing it to you enriched amount, you'd have to launch 10kg, which means you'd have to hit $100/kg launch costs to break even. I'm not convinced that will ever be possible; that's on the order of a first class arline ticket for a 50kg person.
This also doesn't consider what you're getting for launching it into orbit. If the 100 year risk of a casket leaking is (say) x mrads into the environment, you're going to have to consider what the equivalent of vaporizing all of it into the atmosphere in the event of a failed launch is. the fallout (hah) from a failed launch of nuclear waste seems magnitudes more catastrophic than having the same stuff slowly leaking in the middle of a desert cave.