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This works better using the WordPress app.
Open the WordPress app and select "View Admin". If this is the first time you've used it, you'll have to connect it to your blog in "settings" first.
Add a new post, (highlighted in white in the menu on the left) and select "Add Media".
On the media page select "Create Gallery". Now you can select or upload files from your iPad. Check all that you want to include.
Use the "Preview" button to see what you've got, but it's not live until you come back and hit "Publish". Good luck!