Here is what I do that may help you with your first wish.
If I have an item with more than one picture (most all do) I name them the same with a number after each. Ie, pic1, pic2, pic3, etc. When I add my pics to the auction lot I have to do the first one the regular way, the next ones are easier. AW2K defaults back to the directory I got my first pic from when I hit the enter key. (the "add image" button is already highlited) The first pics name is highlited, I hit the right arrow button, hit delete, type the next number, hit enter. I can ad six more pictures about as fast as you can read this.
Just my way around this, for now.
BUT, I agree, being able to add more than one picture at a time would be sweet.

rodgw