It *is* an antiquated OS after all. I know it's the point --- which is why it's annoying that I can't figure it out.
Here's my current thought pattern -- I used the Advanced Config app to set the "My Documents" location to \Storage Card\My Documents\ -- Then, I'm going to do the registry edits to move the pictures from the DCIM location to the \Storage Card\My Documents\My Pictures\ --- *then* in theory it will all sync when I plug it in. That's my theory at least