Deleted iTunes Media off the Mac, Can i now get it to read from my Hard Drive ?

Question

I started looking into this as my Mac was using Roughly 500 of 750 gig on Music. But I've only recently noticed that this is due to duplicates in My Music folder and iTunes Media. Ive done Some reading up and can't seem to find a definitive answer to what to do.
Ive Backed up My Music and iTunes media on a External Hard-drive, My Music folders are all neat and organised and would like it to stay that way, But I've noticed iTunes media folder was a mess, This is My fault as i had the make a copy to iTunes media ticked in preferences. And the other one De-selected ( Keep Music Organised )
So to free up space  on the Mac I'm going to delete iTunes media as this is no use to me the way it is, I can't find anything in there and it looks a mess. The Problem with this is iTunes reads from iTunes media and i would rather it read form my organised Music files on the internal Hard-drive so i can keep ontop of it.
All my Playlists are built within iTunes as i use them in Serato for DJ Purposes , So i would like to keep these playlists and just let iTunes read from the hard drive instead Is there a way once iTunes media is deleted i can highlight a 2014 playlist for example with 250 songs in and change where iTunes looks for them so i don't have to reload all the music? with iTunes media deleted there coming up saying can't Locate File , but i will have to manually show iTunes 25000 where they are manually , Can this be done per Playlist in one big Hit?
Thank you and hope it all made sense

Answer 1

Unfortunately it is not making enough sense for me to try to make real suggestions.
If you are going to disable iTunes media preferences then you have to be 100% organized and know how iTunes works because from that point on iTunes will stop helping you maintain your files in any way.
Yes, it may look a mess but the whole thing is designed so you should never need to look in your iTunes folder yourself, just at the iTunes application window.  Maybe you need to do this to use your Serrato thingy but that's because you're doing something special.
If you add a file to iTunes and have the "copy to" preference set then it will place a copy of what you add in the correct folder inside iTunes Media folder.  The only way you should have media files actually directly in other folders is if you put them there yourself or you have residual structure from pre-iTunes version 9 before media was split into folders of different kinds.
If you disable iTunes media preferences then iTunes is absolutely terrible at following media moved to other drives.  Moving to a different drive is not really moving, it is copying and then deleting the original, and that means iTunes sees the file as being gone.
I really get lost on your fourth paragraph.
What are the iTunes library files? - http://support.apple.com/kb/HT1660 More on iTunes library files and what they do - http://en.wikipedia.org/wiki/ITunes#Media_management What are all those iTunes files? - http://www.macworld.com/article/139974/2009/04/itunes_files.html Where are my iTunes files located? - http://support.apple.com/kb/ht1391 iTunes 9 [and later]: Understanding iTunes Media Organization - http://support.apple.com/kb/ht3847