The situations where there's multiple versions and a decent size to them are pretty much the exact situations where having bot-assisted movement is most useful. It might be mildly annoying to move a single 75 KB image over. It's bloody awful to move 12 images of 36 megabytes each. The maximum move size needs pushed WAY up.
As to how this situation arose: Long story short, I was doing a difficult restoration while copyright status was being worked out on Commons. I uploaded partially-done files as I went. Consensus came down in favour of Commons hosting the file, as the only thing that would give doubt to the status (a partial attribution in an unreliable source to a name that does not appear to have any other known works discoverable, nor any reliable sources that even cover his or her existence) was deemed trumped by the very reliable source (the BnF) that said it was both anonymous and public domain.
Oh, there's also a PNG version of the file. 6 files in the history, 87 megabytes each. What IS the limit, anyway?