Home sharing process causes laptop to crash...?

Question

So, for the last 10 days I have simply been trying to move all of my iTunes stuff from an old Dell Inspiron to a brand new Dell Inspiron.
I have a bit of a unique situation as it's more or less escalated annoyingly over the last couple years, so I will start at the begining:
I have an iPhone 4 that was originally synced with an older model of Dell Insipron laptop. The iPhone is still running iOS 6 becasue there is not enough room on the phone to update to iOS 7 (Since it can't get iOs 8). I recently bought a new laptop, a new Dell Inspiron. My plan was simply to transfer everything from the old Dell to the new Dell, factory reset the iPhone then update it to latest iOS possible, and sync all my music and apps back onto it with the new Dell, leaving it synced to the new Dell.
Both Dells are running the newest version of iTunes and latest Windows Updates available. The old one is running Window's Vista, the new one has Windows 8. I originally thought I'd just put all the music files onto a USB and import them onto the new Dell. This unfortunately doesn't work because a vast majority of the music is protected files as they are off CD's or other means. Thankfully, iTunes has the nifty Home Sharing ability. I authorized both laptops and turned on home sharing on both laptops all with the same iTunes account and it instantly home shared about 90% of all my files. I think the internet connection was lost before the transfer was completed. Now I have about 200 songs left that won't home share.
When I select to import these songs the first time after both laptops restarting it says it requires authorization. I deauthorize and reauthorize both laptops and turn home sharing back on. After this, I can select to import these songs again, this time the process starting but immediately getting 'stuck'. I have fiddled with it enough times to realize that what is going on is as soon as Home sharing between the laptops begins, the older laptop instantaneously freezes and will only come back with a hard reboot (holding the power key). I have even tried running iTunes and the laptop in safe mode with the same problem occurring. The new laptop simply pops up with an error about a timed out connection once the old laptop has completely frozen.
I am quite tech savy, know both my laptops inside and out and have cleared the old laptop of everything unnecessary and turned off all unnecessary processes. The laptop works properly doing everything but Home Sharing, so this has to be a problem with iTunes. I tried Calling Apple Support, only to be told they wont even think about the issue unless I pay for apple care, which I can most definitely not afford right now. Really, I just need this stuff transferred so I can wipe the iPhone so I can update the iOS and have my personal iTunes on my new laptop.
Please can anyone help, I would be so grateful.... iTunes has been nothing but trouble ever since i got my first iPod, and it's not even the products, it's always just the iTunes software on my laptop that causes the issue. I really don't care how I get these protected files off the old laptop onto the new one, I just need help getting them there!
Also a note: I no longer have the majority of the Cd's, etc, that these files came off of... Alot of them now belong to other family members who may well be accross the other side of the country.
Message was edited by: boodles95

Answer 1

Also a note: I no longer have the majority of the Cd's, etc, that these files came off of... Alot of them now belong to other family members who may well be accross the other side of the country.