In case anyone was curious, in regards to #4 (encoding H.264 files), I eventually bit the bullet and upgraded to Quicktime Pro (which kills me, given how much I dislike Quicktime). Anyway, the result is that, unsurprisingly, Quicktime appears to be the only real low-cost solution for encoding H.264. It definitely takes forever (particularly with multi-pass encoding), but the results are great. I'm really only using it so I can encode home videos for viewing in iTunes on my parents' computer. Later on I'm assuming that the iTV will be able to play these files with little effort (am I crazy to think that?).

The one thing that's annoying me? iTunes. When I import an H.264 MOV file, iTunes automatically takes a frame out of the first five seconds and makes it the file's artwork. That's fine as a placeholder, but for some reason it appears to be completely impossible to change the artwork to something else! It's driving me nuts! I did what you would assume you'd do, I went to "Get Info", Artwork tab, and then looked for a way to change it. But the "Add" and "Delete buttons were grayed out, and the only right-click option I have is Copy. Can anyone help?