A few people suggested Kitashi's Art Gallery Manager based on my last journal, and while it doesn't do exactly what I want (automatically download all the submissions with comments from my gallery), it looked neat enough to give it a shot for uploading.
Thing is, I can't get the damned thing to do anything I want except download existing galleries. I added 3 accounts to it, but now it won't let me add any more "Adding account failed; Could not create account with information given"
On top of that, gallery management doesn't seem to work, and I'll be damned if I understand how to upload anything new, so does anyone have any guides on how to get this program to cooperate? I would also accept a viable alternative with a better GUI. There's practically no support for this program and I'm getting extremely frustrated with it.
I ended up using WaxPost to update my Weasyl page, but I'm looking for a more automated solution for other things, like I might need to migrate my wife's stuff to Weasyl at some point, since she's expressed interest in doing silly comics again.