How do you download music from a Windows XP to

You can simply connect the external HD to a Mac. Mac can read NTFS disk and read/write FAT32 disk. You than open iTunes, do File->Add to Library, and select whatever WAV files you would like to add from the external HD.

"Add to Library" will copy WAV files into iTunes library unchanged. You can than convert the WAV files to AIFF or any other format iTunes supports inside iTunes.

Another way to do this is to use a free program call Max running on OS/X. Max can convert almost any audio format to any other audio format and insert them directly into iTunes library. I use it to convert FLAC file to Apple Lossless. It works very well.

Max can be found here:
http://www.versiontracker.com/dyn/moreinfo/macosx/28353

I am using a MAC and have the latest edition of iTunes. What does it mean that Mac can read "NTFS disk and read/write FAT32 disk? I get the rest of the comments . . which I appreciate.

To clear it up further, the plan is buy a Drobo with sufficient capability to handle about 3500 CDs which will come in as wav. Since the Mac can't handle that much memory by itself, should I assume that most of this music will have to be pulled directly from the Drobo for listening? What about album artwork?

I have just started another thread to find out how to "upgrade" my existing album artwork in iTunes. Some of it is crystal clear and some of it looks like I have cataracts. I can't delete the bad artwork without deleting all of the music as well.

Many thanks to each of you so far that offered advice.

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.