I think it's never necessary to insert more than one item. Just looking at the last opened environment and inserting one item if necessary should suffice. The only problem would be:
Ok, thanks ;) The second example is still not fixed, that requires checking for items on the same line, but I don't think it's necessary to spend time on it.
When multiple itemizes are opened, multiple items are inserted.
I think it's never necessary to insert more than one item. Just looking at the last opened environment and inserting one item if necessary should suffice. The only problem would be: