This is an old thread, but I thought I'd bump it because I would like to upload from my Mac (or Win - I have XP running on my Mac too) to TiVo. Heck, if you can download content from your TiVo to put on an iPod, and you can have podcasts directly on the TiVo, why not upload non DRM-enabled videos? It'd be nice to upload videos of my 9 month old for easy playback when people come over, or even videos from work to demonstrate our augmented reality technology.