IPhone – Photos not deleting off iPad when deleted from iPhone

Photo Stream definitively only works for photos (or screenshots) taken after it was enabled.

As for your other problem: Yes, if you are logged into the same iCloud account on both devices and have Photo Stream enabled it should sync whenever you are logged in into a Wi-Fi environment (apparently Photo Stream doesn't sync over 3G).

What else can you try:

• Take a screenshot on the iPad, make sure you are in a Wi-Fi environment and see whether the screenshot appears on the iPhone
• Log in to iCloud from your computer (requires Lion or a recent Windows version of course) and see whether the photos get streamed there

Try Unbound app. It uses dropbox to allow you to organize your photos on your ipad. So you can move, delete and rename photos on your iPad and the changes are synced back to your dropbox.

I tried it and liked it, but I don't use it, because all the managing functions (move, delete, rename) only work, when you are online.