Creating a droplet from a snapshot should retain all the data that was on the original droplet since the whole disk is copied. Have you created the new droplet immediately after taking the snapshot or have you changed anything on the original droplet before creating the new one?

Ah, good point, maybe I had added after the fact, checking date of image confirms that fact.

Any thought on the moving files between droplets, is there a better way then downloading and uploading?

I recently needed to transfer a large database (~3 GB ) from one server to another. The source server had apache2 running, so I just used wget to get the file onto the other droplet. took me about 30 seconds, at 105 MBpS ;)