I'm not a Mac user, so I'm afraid I'm not going to be too much help. But as far as album art size, I can tell you that I have a few that are 500x500 in size, and the player shows them with no problem. I don't know if the actual file size matters or not, but because my previous player could not handle album art files larger than 31kb, all of my files are below that size. Regarding playlists, I am able to generate and successfully transfer playlists using Winamp (which, as far as I'm aware, is not Mac compatible, but at least you know it can be done outside of WMP).
