not enough posts for a picture

i guess that you need 10 posts for a picture to show up if you post it. if i posted a picture before i had 10 posts, will it automatically show up when i hit 10 posts, or will i have to re-post it?

now when i try to upload, it says that 'upload failed'

It's possible that it is too large to accept it from your computer. I used to get the same thing sometimes, so I ended up using my Flickr account, and linking the picture from there.