Usually I upload my photos through media library then insert those photos into a post. When I insert photos into the post, through "insert photo" then "media library", I can use the check boxes next to the photos to insert several photos at once.
WordPress uploads the photos in chronological order (1, 2, 3, etc.) but then when I go to insert the photos in the post, they appear in reverse chronological order (3, 2, 1, etc.). The only "solution" I can figure out is to upload the photos in reverse chronological order (or just tolerate it as is), but either option is quite a nuisance. Is there any other way to change this?