1. Not without some sort of code modification as that is not an option to show there.
2. Simply put thats a feature in a graphics program for a home computer which is out of scope on a server's image processor. The processor can only resize an image to dimensions you state in the program setup. The program can crop a thumbnail from the center. But letting a user select some hand drawn area is not a part of things.
3. All guests are tracked by IP. There is no username entered it will show as Unregistered on the posts.