How do you download music from a Windows XP to

Puerto, that means Mac can at least read your Windows formated external HD so that you can just connect the HD to Mac. You don't need to take any extra step to transfer files between Windows and Mac.

You can store everything iTunes needs on an external HD. In fact that is exactly what I did. It is very simple to do on Mac. All you need to do is to make an alias for the external HD, rename it to iTunes, copy everything from your old iTunds folder (which is inside the Music folder) to the external HD, delete the old iTunes folder, and drag the alias into the Music folder.

From now on, iTunes will treat the external HD like the old iTunes folder and store and read everything there.

Got it Sidssp: As soon as I get the Drobo I will make the switch from the Cavalry HD to the Drobo and give the Cavalry to my friend for downloading his stuff to me. I presume that I will then bring "his music" into iTunes from the Cavalry, make the conversion from wav. to aiff. and then download the converted files back out of iTunes into the new Drobo along with my existing library.

Here's the other question though: Will my friend's artwork come with the music and if so, when I pull music from the new Drobo will the artwork come up on the screen?

Since the "new library" will consume WAY more memory than my Mac, I assume that from now on I would be pulling music directly from the Drobo and not the internal memory of the iMac.

Actually the steps will be bring the WAV files from Cavalry into iTunes by means of iTunes' "Add to Library..." menu, convert WAV files to AIFF inside iTunes, and finally delete the WAV files from iTunes.

WAV file is not capable of storing artwork. Your friend will have to keep the artwork in separate graphic file like jpg. You will have to add the artwork manually following the steps in the other post.

Drobo has nothing to do with the internal memory of iMac. iTunes always pulls music from your hard drive and only uses as much internal memory as needed for it to run.

SIDSSP: Thank you for the easy to understand responses. Let me rephrase my last question - I don't think I was very clear.

My friend's library will consume well over 1TB of memory. My iMac has a 500GB capacity. Right now, all of my library (about 360 GB) is stored in the iMac memory AND on the Cavalry Ext. HD as a backup. When the new, bigger, library comes in, the iMac memory won't be able to handle it all so it will ALL go to the Drobo. Does this mean that when I play music that the Drobo will have to be on so that iTunes can access the music? (sounds like a really dumb question right now) If so, there would be no further point in keeping any music stored in the iMac internal HD, correct? IMac would, as you indicated, use only enough HD capacity to run iTunes and play the album.

Once the files are converted to aiff. presumably I could add the artwork and that also would be stored in the Drobo and be displayed via iTunes when an album is "called up" from the Drobo.