Q: NEW User - Keep Files Intact?

You will have to manually manage your music which has certain disadvantages but will keep your structure. Go to iTunes > Preferences > advanced and one of the options will be checked to have iTunes organize your media. De-select this.  You may also wish to uncheck having iTunes place a copy of files in media folder when adding files.

I use iTunes on a Mac and as long as the files are kept on the same drive as the rest of the library files (in the iTunes folder) the the application is good at keeping track of them. I recall a PC user saying this was not the case with Windows but you will just have to check as you go.  Bear in mind that neither system has a way for iTunes to easily track files moved between drives unless you are moving entire libraries across.

My understanding is if an album was previous labeled "unknown" and you give it a name in the iTunes window the file will be moved to a folder in albums with the new name. I have been manually managing my media myself for 15+ years so you'll excuse me if I don't change that setting and try just to see what happens.

 

Folder called "The_Script" with a single mp3 titled "Hall Of Fame".  I throw it (folder containing the file) into the Automatically Add to iTunes folder and it does, but into that void

Yikes!  To achieve what you want to do, you must not use the Automatically Add folder.  It will immediately whisk the file to the iTunes-preferred structure, messing up the structure you have spent years curating.

As Limnos suggests, go to Preferences > Advanced and make sure that "Keep..." and "Copy..." are both turned off.  Then any files/folders you add to iTunes will stay where they are.  And when you add them, do so via File > Add File/Folder to Library, so that Automatically Add will not have its evil chance to auto-magically rearrange them.

Take a look at Getting iTunes & Windows Media Player to play nicely. The same general rules apply for Winamp. If you can set out your media the way you want it but inside the iTunes Media folder, ideally with music inside iTunes Media\Music, then you can set up iTunes so it doesn't move things around and your library will be able to carry on working as and when you need to move it to a new drive or computer.

tt2

Following up Limnos's and Ed's comments ... while you can retain your own file and folder structure, it actually takes both more work and more understanding of how iTunes functions to do so.  First, even with the "Copy files ..." option turned off this only applies to two of the ways you can add media to iTunes.  The interaction of the "Copy files ..." setting and different addition methods is as follow:

So if you want to retain your own structure you are limited to the last two methods.  CD imports, iTunes Store purchases, and use of the Automatically Add to iTunes folder (which is used by some 3rd party applications such as Amazon Music) will always place media in the standard iTunes folder structure.

Second, as you've observed when noting that some of your media is shown in iTunes as "Unknown Artist" / "Unknown Album", iTunes is metadata-driven and uses the values of properties or "tags" within media files to populate its database when you add new songs to your library - it does not make use of any information derived from file or folder names.  Steve MacGuire (aka turingtest2) maintains a page of useful iTunes scripts for Windows that includes several that can be used or adapted to derive metadata from file or folder names.

However, you need to recognize that to maintain your own folder structure, file names, etc. involves fighting against iTunes rather than working with it.  If you're prepared to take the leap and allow iTunes to manage your media files for you I believe that you'll find this both easier and more flexible.  One quick example of the latter taken from one of your screenshots: its easy in iTunes to have "Marvin Gaye" as an Artist value but to have "Gaye, Marvin" as the associated Sort Artist value - something you'll never be able to do with an external file/folder naming scheme.

Think of it this way...

All your system files are managed by the OS.

You don’t care where they are. The OS does everything.

iTunes is a database.

When you use a database, it’s to help you manage data/info.

You don’t worry about where all the individual bits are, The database takes care of it. Same as the OS.

That’s why you use a database.