Following Henry's problems with the gallery upload, I had a look around for a better solution. I haven't tried it myself yet, but to make uploading images to the gallery it may be possible to use the following program:
http://gallery.menalto.com/wiki/Gallery_Remote
You install it on your computer and it'll do all the rotation, resizing etc on your computer so you don't have to faff with that and can upload lots of pictures in one go. I've no idea how easy it is (it wont be as slick as facebook I'm sure) but if someone want to give it a try then do.