How to upload several images & automatically create an entry for each one?
I was going to suggest using the very handy Import plugin, but I see that it only supports entries, categories, and users. And unfortunately, I don't see another plugin that does this specifically. But have a look at the craft plugins page in case I missed something. 

You might also be able to extend the Import plugin (with permission of course) to support assets. I would guess that it would be a similar process. This could potentially allow you to create a CSV file and import it... then upload the images into the location defined in your csv.