If the "Insert Image" button works, there'll be a picture of a rose on here. I can't see it now, but hopefully it'll show up when I submit the post.......
You obviously know what button to click on (Insert Image), so that's cool. What have you resized your pics to? Keep it at around 1024 x 768 and you should be good to go. When you see your file in the little box, press the 'Upload File' button at the bottom and she'll upload.