Hi!
Long time no visit - but I have both the iLiad and the Reader, and until the iLiad folks sign a deal for DRM content, the Reader is a better purchase for ebooks - unless you're into various classics available for the iLiad at manybooks.com. If your aim is to read PDF's, I think both readers work allright - but the larger screen and greyscale might suit you better if want to pay the money for the iLiad.
I've found it equally easy to copy PDF's to both devices. There's a little fiddling to do if you want to match the screen dimensions perfectly - but if I can do it anyone can.
Larry Z.