2014 Sync problems on iPod classic / Please help!! 2014

Question

Hello community!
I really need some help with this problem I am having... I have done some research for the past few days on my own but nothing I have found has helped.
First some specs on my device...
iPod Classic: 80 GB (I believe this is iPod with video, assumed on the fact that it supports movie syncs)
iPod software version: 1.1.2 (up to date according to iTunes)
Formatted for Windows
Syncing to Dell Inspiron with Windows 7
iTunes updated to current version (11.4)
I had much mof my music library uploaded onto my iPod for quite sometime. (close to 14,000 songs synced at 192 kbps) I often like to put my iPod on shuffle and just listen to whatever comes on, but here and there I will skip songs until something I am in the mood for comes on... I began to notice that my iPod was freezing (ON THE DISPLAY ONLY!!! Playback through speakers continued) when I would skip through songs... Once the screen dimmed however, I could once again skip to the next song. I figured this was a problem concerning corrupted files or something similar. These are the steps I took..
1.) Updated iTunes to version 11.4 and checked for further updates
2.) ATTEMPTED to check disk within Windows (was unsuccessful and heard the iPod making a lot of 'clicking' noises from within the casing)
3.) Performed an iPod restore within iTunes
4.) Performed a check disk within Windows and recovered any bad sectors (SUCCESSFUL)
5.) Selected 'Music' sync and the option for 'Entire music library'
6.) UNCHECKED 'Include music videos'
7.) Reconfigured settings as they were before and made slight changes..
     a.) Checked 'Open iTunes when this iPod is connected'
     b.) Checked 'Sync only checked songs and videos'
     c.) Checked 'Convert higher bit rate songs to '192 kbps' AAC'
     d.) Unchecked 'Manually manage music and videos'
     e.) Unchecked 'Enable disk use'
8.) Began a sync on my iPod... With well over 10,000 songs I knew this was going to be a lengthy process.. I left computer unattended..
When I returned to my computer, iTunes was unresponsive... The only way I could get iTunes to show was to minimize a Window on top of iTunes. iTunes states 'Syncing iPod... Do not disconnect' but does not show a rolling progress bar.. I cannot cancel sync, I cannot eject iPod, I cannot close iTunes...
I attempt to eject iPod device through windows, UNSUCCESSFUL (Cannot unmount generic volume while the device is in use)
I 'Ctrl+Alt+Dlt' to Task Manager and End Program 'iTunes' UNSUCCESSFUL..
I End Process 'iTunes.exe *32' and eject iPod through Windows SUCCESSFUL
When the iPod displayed 'OK to disconnect with load bar, I disconnected the device.
As soon as this bar was full iPod IMMEDIATELY rebooted completely and powered back up with only 20 songs synced. (Frustration ensues)
Confused and thinking maybe my screen saver caused an interruption during the sync, I changed screen saver and power saving options to eliminate any possible interruption, REPEATED STEPS 3-8 ABOVE, and started sync again.. Left computer unattended
Again, coming back to computer much later, iTunes was in the same unresponsive state. Closed iTunes and began looking for answers on the internet. Any and all answers I found stated I should restore iPod, update iTunes, run diagnostics tests, etc., etc...
All of which I had done EXCEPT for running a diagnostics test..
Running a diagnostics test: I ran only the tests concerned with 'Device Connectivity' and 'Device sync' tests.. Here are the very interesting results I yielded from these tests...
Device Connectivity Test:
Support services:
     'iPod support service is running.' Status: GREEN
     'iTunes Helper is running.' Status: GREEN
     'Apple Mobile Device is running.' Status: GREEN
Ports:
     'USB ports verified.' Status: GREEN
     'No FireWire (IEEE 1394) ports found.' Status: GREEN
     'iPod found.' Status GREEN
ALL TESTS PASSED
Device Sync Tests
Results:
     No iPod touch, iPhone, or iPad found. Status: RED
ONE OR MORE TESTS FAILED
I am at a loss, I realize that Apple has discontinued the iPod Classic but does that mean iTunes will no longer support these devices!?
And if ANYONE has ANY suggestions for possible steps I can take to regain syncing privileges to my iPod once again, please let me know!
Also, I have diagnostics test results saved on my desktop and available to post if required!
Thank you for any and all help!
-Chris

Answer 1

!UPDATE!
I made several adjustments to my sync options and made some progress and am now trying to sync in 'stages' as I like to think of them.
Here is what I did:
1.) Under 'Music' tab in 'My iPod' options I opted to sync 'Selected playlists, artists, albums, and genres'
2.) Selected a small portion of tunes I know I want on my iPod (ended up being close to 3,500 songs.
3.) Under 'Summary' tab I unchecked the 'Sync only checked songs and videos' box
4.) Unchecked 'Convert higher bit rate songs to ___ AAC'
5.) Checked 'Enable disk use'
6.) Ran a SUCCESSFUL sync!
I am now running a sync keeping the same adjustments in place and have added 6,556 songs. (SYNC IN PROGRESS)
I am wondering if trying to convert that many songs to a lower bit rate is causing sync problems and it appears as if I am at least making progress on this. HOWEVER, I really prefer to decrease the bit rate on my songs so I may fit more on my iPod... Usually most of the files I have in iTunes are at 320 kbps with a select few at 192 kbps. I would like to make everything the way it was before my first iPod restore.. 192 kbps, but this also seems to be the cause of the sync problems I am having? Anyone else have a comment on this?
Thanks again
-Chris