Jeff,
I am not trying to take CW or Jamos place answering this, but since I have already ran into it, yes, taking pictures out of the gallery or deleting any attachments will just leave a box with a red X in the post you had the picture in. If you know what posts you have pictures in that are important, once you reload the gallery you can then go edit the post and put the new URL of the picture in and it will be back. If you have a lot of them that would not be a very practical option, but since I only had a few that is what I did. I have been removing pictures and attachments for the past month and now have mine pared down to a low value.
Ron