Pardon if this question has been answered already but I couldn't find it on the forums or searching for it online.

I've only had BB for a few days and am still learning my way thru its functions, and here's what I'm hoping to find an answer to. I currently have my media on my Mac's computer's HDD and am thinking of moving it all to an external HDD connected to BB. I would like to have copy of the music stored locally so 1) I can play it whenever I'm away from home and more importantly 2) so I can sync my music with my iPhone. What's the most painless way of accomplishing this?

For music files, I will store the high-quality original files on the external HDD and want to have lower quality (say 192kbs) on my HDD (and then to my iPhone). What solutions have folks come up with?

Is there a way to effortlessly transfer new files to the external HDD? Is there a way to automatically sync the the external and contents of the local HDD (ie. iTunes library)?

Apologies if I'm not too clear.