Image Upload, PDF Upload and Custom Post Order

Hi, having downloaded Custompress for the first time I have three specific requirements and am hoping to get a 'yes', 'no' or 'this is how' for each of these 3 issues if possible. Any help would be greatly appreciated:

(1) The ability to add 2 images to a custom post. The first one on a page that shows a summary of each custom post within a taxonomy and the next one a 'detail' page showing the full custom post.

(2) The ability to upload a PDF specification doc to the full post page for download.

(3) The ability to set a specific order of appearance for the custom posts, so rather that alphabetically or my date, an order of my choice.

Thanks in advance.