TT2,
I appreciate your input, but my intent was to tell you that on the Mac side, iTunes does not always behave as you have said. I was not specifically looking for a solution this time. I did not realize your iTunes experience was on the PC side. They do have their differences.
Let me start off by saying, I won't be making any changes while I am trying out 10.9 on an external drive, and have 10.7.5 on the Mac HD. Everytime I switch between them, it seems to want to reorganize the library and change the path.
I have lived with this problem for years, and have resigned myself to having to manually organize the library. With iTunes 11.1, I spent hours on the phone with several Senior Apple Advisors working on a sync issue, and we have reviewed my iTunes set up in minute detail, with me beating them to the punch on issue/ cause/ solution time and again.
We have gone over Organize and Rearrange in the past. iTunes has churned the library time and time again, and keeps turning on "Keep iTunes Media folder organized".
I said nothing recently about a wrong path, but since I keep my library on a external Drobo, so the path I want in iTunes > Preferences > Advanced is /Volumes/Doc/Music/iTunes/iTunes Media and not /Users/brent/Music/iTunes/iTunes Media.
I have also seen this to some extent with music, also. When I manually organized it, I had music both inside and outside of where it should have been, with a few artist having folders in both.
I recently decided to turn off Keep Organized, since it have never worked for me.
If iTunes can not access the Drobo, it will switch the path to on the Mac HD. iTunes 11.1.2, in OS X 10.7.5, has doing a much better job of not doing this, until I started testing and booting from an external HD with 10.9. It has been changing the path and turning on Keep Organized.
I have not wanted my iTunes library on my Mac hard drive since about 2006. It had been external to the Mac HD, either on an internal RAID or external Drobo. I have been fighting the issues of having a remote library for years. Added with the occasional lose of content from iTunes. I have about 113 GB of audiobooks and only about 18 GB of music. I have taken to keeping the audiobooks below Music, and even with iTunes. And most of the time iTunes finds them without a problem.
I used your Music vs Media chart to manually organize it. And the first audiobook that I imported was put in the wrong place.
I have never seen the sturcture you show above include the [[D-[## ]]<Name>.<Ext> portion. On a Mac it has been <Media Folder>/Audiobooks/<Author>/(Title)/ (possibly book part name). Remember that importing from audio disc will always put it into Music and you have to Get Info and change the media to Audiobook. For 90% of audiobooks imported from disc, putting them all in a single flat folder (I understand that to mean a single hierarchical level folder.) will horribly put them out of order. Since it seems the publishers purposely title the small segments so they will not play in order if imported into a single folder.
For now, I am going to put this issue on hold, and test 10.9 and other issues.
Thank you for your input, it is appreciated.