Having trouble moving iTunes music onto iPhone 5

Question

Hey guys,
I'm going to try my best to clarify everything so please bare with me.
Windows 7 (64-bit)
iTunes (11.3)
iPhone 5 64GB (iOS 7.1.2)
- All are up to date as of now
- There is enough storage for my 4,462 songs I want to add
Yesterday, I finally transferred all of my music from my library on my computer to this one (and downloaded some new songs).
I wanted to put all of my iTunes music from my computer onto to my iPhone via USB cable. I wanted to delete all music from my iPhone to clean the slate then add the new music to make sure everything is new (no duplicates, wrong songs, etc.) I have done this a few times before.
So I plugged in my iPhone and checked manually manage music (as I usually do), then highlighted all of my songs on my iPhone and deleted them. Then they disappeared from the phone's music list and showed that I had gained all that space back (this is all normal).
So I highlighted all of the music on my iTunes (4,462 songs) and dragged them into the iPhone music area.
It then began copying the songs over, so I left it there to copy overnight because all of those songs would take a while to transfer.
Today I woke up and checked to see if it was done and I saw that most songs did not copy and instead were grayed out with the dotted circles next to them.
It said "Copying 1 of 382 --> Song name" but hasn't made any progress since then.
So I deleted the grayed out songs from the list but couldn't delete the ones that were trying to copy.
I tried cancelling the copying process but it was stuck at that same "1 of 382" for 30 minutes.
So I ejected my iPhone but it said "Syncing iPhone" or something like that. I left it like that for 10 minutes and it didn't do anything so I unplugged my phone from my computer and did a hard restart on the phone. In the meantime iTunes said something like "Failed, the device was disconnected."
I restarted my computer and opened iTunes again and connected my phone again. I plugged in my phone and tried syncing all of the music instead and it did basically the same thing and then said there wasn't enough room to transfer items.
I didn't understand because when I clicked on my iPhone device it didn't show any music. But then I looked at the storage bar and it showed that music was taking up about 30GB (about the amount of music that I wanted to transfer originally) on my iPhone.
So now I'm trying to delete the music off of my iPhone but it doesn't show the songs on it in iTunes.
I tried deleting all the music through the options in my phone (it let me do it) but it didn't delete any music (even after hard restarting my phone).
So now I'm not able to transfer music to my phone...
     1. Because it says there is not enough room
     2. I'm having trouble with the songs that won't transfer via syncing or manually managing items because of the stupid
I've tried so many things, read so many threads online but nothing is working, and I definitely don't want to restore my iPhone...
     1. Many people said they've tried that and many other things but nothing worked
     2. I don't want to have to bother with that whole process and am worried about losing something(s) in the backup process.
If anyone has any suggestions, I'd much appreciate it them.

Answer 1

I haven't, I've been using the same account since I first got an iPod. Although...I just noticed that all the songs that did transfer are songs I bought from iTunes. None of the songs I imported from CDs got transferred. What's the deal?