I have my iTunes Library on and external hard drive. I have a new computer and want to use iTunes and KEEP my files on the external drive.

Question

My iTunes library is on an external hard drive, and I was able to access / add to the library from my windows laptop.
I now have a new laptop, and want to be able to KEEP the library on the external drive while being able to use iTunes from the new laptop.
I have selected "choose library" in iTunes, and have chosen the iTunes Library.itl file on the external drive.
My media populates in iTunes on the new laptop version of iTunes, but when I click on a song iTunes says that it cannot locate the song.
Your help is kindly appreciated!

Answer 1

Thanks.  Were the settings shown in your last screenshot in force when you added the song that's shown on being on the C: drive?  It is also possible that at some point you ran iTunes with the external drive disconnected, in which case it will have defaulted to the library on the C: drive, or that you've run iTunes without explicitly selecting the library on the E: drive.  To make sure the latter is the case, hold down SHIFT while starting iTunes, then when you get this prompt:
click on Choose Library..., navigate to the location of your current iTunes Library.itl file, and click Open.
Part of your issue may that its not obvious where that current database file is located.  The folder layout on your E: drive isn't the one that's most easily managed - so its possible that the database file could be in:
E:\xxxx\Files\iTunes
E:\xxxx\Files\iTunes\iTunes
E:\xxxx\Files\iTunes\iTunes 1
I suggest that a lot of your issues can be addressed by reshaping your library into the reliable "portable" layout as described in tt2's Make a split library portable user tip.  Comparing your screenshot with the equivalent on my system (where I have a "well-formed" library on an external drive):
where:
there is just one iTunes folder with everything used by iTunes inside it
all media is held within subfolders of the iTunes Media folder
The way you have yours set up, where the iTunes Media Folder location is set to E:\xxxx\Files\iTunes rather than E:\xxxx\Files\iTunes\iTunes Media is probably why some of your media is not being located correctly - the extent to which iTunes can correctly resolve locations is, to an extent, reliant on the folders for the different media kinds (Music, Audiobooks, etc.) being inside the iTunes Media media folder.  One common misunderstanding (not helped at all by Apple's documentation!) is that the iTunes Media Folder location setting in Edit > Preferences > Advanced does not tell iTunes where to find anything; rather it determines where iTunes will put new additions to your Library, in conjunction with the Copy files to iTunes Media folder ... flag:
I would definitely take the time to work through the steps to bring your library into the "portable" shape - there may be few remaining issues with broken links when that's complete but this will be much easier to fix if your library is in a more standard structure.