I need help transferring music from old PC to iPhone

Ok...I apologize in advance for the length of this post, but I have tried everything and my husband is no longer amused!
His iTunes account was created many years ago with an iPod Nano. I don't even remember which computer I had at the time and do not think I still have the original. The majority of his music is ripped from CD's. When Verizon finally got the iPhone, he got one immediately. I remember having to download the Pod to PC software at some point to move music from the iPod to a new computer. For some reason, I think the original crashed? (I don't know if this is relevant) Anyway, I think it was easy to originally put the music on the new phone.
At some point, however, it was lost from the phone. And, then that phone was dropped and the glass broken. He bought another from a friend. The current one has only the purchased music that is in his iCloud account.
Now, this is my issue. I have an old Toshiba Laptop that appears to have all of the music in the iTunes library. However, when I plug in the iPhone (which is a 4 by the way, but has been updated) it does not even recognize that it's plugged in. and, nothing I can do seems to allow me to update iTunes to a more current version. I'm sure this is the computer itself as it is barely hanging on. (and never used!)
I also believe that the old iPhone still has the music on it, but I can't be sure as the screen is so badly cracked that I can't access it.
So: two questions: Can I some how get the files off of the old computer and transfer them to the iPad and then push them to the phone? Say, with a flash drive or drop box or iCloud?
OR: should I just take the old phone and plug it into my computer (a Macbook Pro)... but if this is the way to do it... how exactly do I have two iTunes accounts and libraries on one computer? I'm sure this is going to be the most suggested option, but honestly, I would prefer to not do it this way if there is another option.
Any help that you can offer will be so very appreciated as I have wasted a lot of time trying to figure this all out!

st double checked and all of the folders are in the new computer. I can see the whole library in iTunes on the new computer but when you click on a song, it states that "The original file could not be found. Would you like to locate it?

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Edited by an Apple Discussions Host

I need help transferring music from old PC to iPhone

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