I knew this was the way this behaved, and was prepared to deal with it, but I think it's pretty funny that no one's sure if the behavior we're seeing is a bug or a feature.
I've only had real troubles with this when trying to move sections of pages around inside Lessons. Let's say I've determined a page in a Lesson is too long, or covers too many topics, so I want to break it up into 3 pages. In 1.9, I would've gone into the editor and open up the HTML and copy and paste the final 2/3 into Notepad, then make 2 additional pages, and copy and paste half of the html into one page, half in the other. Unfortunately, in 2.0 I can no longer do this without having to reinsert all of the images into the second pages.
I have found this type of manipulation happens all of the time among the teachers I deal with in Moodle.
I have ALSO found that updating a picture that's used multiple times happens all of the time among the teachers I deal with.
I'm not sure I prefer the 1.9 model over the 2.0 model, but 2.0 certainly has some quirks I do not enjoy.