ITunes to iPod Sync corrupts iPod Music Library - Data Usage Chart Incorrect

Issue 1: Syncing Music Library
Issue 2: Data Usage Sync Displaying Incorrect Data
Conflicting Device: iPod Touch (5th Gen- Model MD717LL/A- 32GB)
Conflicting Device OS: iOS 7.0.4 (11B554a)
Capacity of Device: 28.01 GB
Current (As of February 18, 2014 at 11:30 PM EST) Total Space Used on Device: 19.05 GB
Current (As of February 18, 2014 at 11:30 PM EST) Total Space Available on Device: 8.95 GB
Conflicting Device 2: iTunes for Windows Vista (iTunes 11.1.4.62)
Back Up Config: iCloud
Option(s) selected on iTunes (in iPod Menu):
-Sync with this iPod over Wi-Fi
-Sync Music
     -Entire Music Library
     -Include Music Videos
     -Include Voice Memos
-Sync Movies
-Sync TV Shows
Number of Songs in iTunes Library: 1245
Number of Songs in iPod Library: 1395
Note on Previous Data: This is due to errors with purchased songs from iTunes. I have a downloaded version of the purchased songs with added lyrics as well as a iTunes download for a fresh version of the song (has the cloud icon next to them).
Mutual Step(s) Leading to Issue(s):
- 1 - Open iTunes
Individual Step(s) Leading to Issue 1:
- 2 - Alter, Add, Change, Remove, or Edit any Music in my iTunes library
- 3 - Connect to iPod either via lightning to USB cable or Wi-Fi
- 4 - Click on the "iPod" button on the Navigation Bar
- 5 - Click "Sync" at the bottom of the screen
Individual Step(s) Leading to Issue 2:
Issue: Syncing Music Library
Issue 2: Data Usage Sync Displaying Incorrect Data
Conflicting Device: iPod Touch (5th Gen- Model MD717LL/A- 32GB)
Conflicting Device OS: iOS 7.0.4 (11B554a)
Conflicting Device 2: iTunes for Windows Vista (iTunes 11.1.4.62)
Back Up Config: iCloud
Option(s) selected on iTunes (in iPod Menu):
-Sync with this iPod over Wi-Fi
-Sync Music
     -Entire Music Library
     -Include Music Videos
     -Include Voice Memos
-Sync Movies
-Sync TV Shows
Number of Songs in iTunes Library: 1245
Number of Songs in iPod Library: 1395
Note on Previous Data: This is due to errors with purchased songs from iTunes. I have a downloaded version of the purchased songs with added lyrics as well as a iTunes download for a fresh version of the song (has the cloud icon next to them).
Mutual Step(s) Leading to Issue(s):
- 1 - Open iTunes
Individual Step(s) Leading to Issue 1:
- 2 - Alter, Add, Change, Remove, or Edit any Music in my iTunes library
- 3 - Connect to iPod either via lightning to USB cable or iCloud
- 4 - Click on the "iPod" button on the Navigation Bar
- 5 - Click "Sync" at the bottom of the screen
Individual Step(s) Leading to Issue 2:
- 2 - Connect to iPod either via lightning to USB cable or iCloud
- 3 - Click on the "iPod" button on the Navigation Bar
- 4 - Hover over data usage bar
Description of Issue 1:
-When following steps, sync completes by corrupting all music files on the iPod Touch and not syncing altered/changed/added/removed/edited music with iPod.
-All music is either not shown or greyed out/inaccessible.
-When tapping a seemingly accessible song after sync, song immediately skips to next seemingly playable song. This process repeats until all songs are skipped. After the song is skipped, the song is grayed out/inaccessible. A download circle eventually shows showing the process of downloading the music file again. The file is never downloaded and remains stuck at 0% downloaded.
-Music purchased from iTunes is shown as downloadable and will download properly from iTunes if clicked on
-No known cause
Description of Issue 2:
-When looking at the data usage bar for my iPod Touch the status shows approx. 512 Mbs of data over capacity of the iPod and all data shown is categorizes as "Other"
-No known cause
-Causes Sync to Fail
-No Other Symptoms Seen
Affected Functions with Issue 1:
-Music Playback on iPod Touch
-Playlist Creation on iPod Touch
-Successful Sync Process
Affected Functions with Issue 2:
-Proper and Valid Sync with iPod
Failed Attempted Fixes for Issue 1:
-Restart of iPod
-Restart of iTunes
-Restart of Computer
-Hard Reboot of iPod
-All Combinations of listings above
-Multiple Syncs
-Ejecting iPod-> Removing USB from Port-> Connecting USB to Port again
-Deselecting "Sync over Wi-Fi with this iPod" option-> Clicking "Apply"
-Trying all of the above with and without the Music app running (including in the background).
Failed Attempted Fixes for Issue 2:
-Restart of iPod
-Restart of iTunes
-Restart of Computer
-Hard Reboot of iPod
-All Combinations of listings above
-Multiple Syncs
-Ejecting iPod-> Removing USB from Port-> Connecting USB to Port again
-Deselecting "Sync over Wi-Fi with this iPod" option-> Clicking "Apply"
Successful Attempted Fixes for Issue 1:
- 1 - Open iTunes
- 2 - Connect to iPod either via lightning to USB cable or iCloud
- 3 - Click on the "iPod" button on the Navigation Bar
- 4 - Navigate to the "Music" Tab on the Navigation Bar
- 5 - Deselect "Sync Music"
- 6 - When pop-up comes up click "Remove"
- 7 - Click "Sync"
- 8 - Wait for Sync to Finish
- 9 - Reboot iPod
- 10 - Reselect "Sync Music"
- 11 - Click Sync
- 12 - Wait for Sync to Finish
Successful Attempted Fixes for Issue 2: N/A
Unattempted Known Fixes for Issue 1:
-iTunes Match (I do not want to pay extra for this service)
Unattempted Known Fixes for Issue 2:
N/A
Annoyances of Issue 1:
-Having to delete all songs and redownload all songs onto iPod, it's very time consuming and frustrating due to the fact this doesn't always work.
-Having every song I bought on iTunes show twice- one downloaded with lyrics and one not downloaded without lyrics.
Annoyances of Issue 2: Disrupts the iPod Sync process (does not let it complete or even start- no error messages occur though) and I am unable to see the proper state of my iPod.
After Effects for Issue 1: A copy of any song purchased off of the iTunes Store is
After Effects for Issue 2: N/A
Occurrence Rate of Issue 1: Every Sync
Occurrence Rate of Issue 2: Occasionally during sync or daily iPod status check.
Origin Date of Issue 1: January 1, 2014 was the first noticed occurrence of this.
Origin Date of Issue 2: January 1, 2014 was the first noticed occurrence of this.
Note: If there is anything else needed please tell me- I would like to find a better solution or have this turned in as a bug. Thank you for your help!

Were you ever able to solve this problem? If so,
how? If not, did you see the same slowness copying
the files in Windows Explorer from the NAS to the
iPod?
No I wasn't. To be honest I have essentially given up as even if I can fix it, disk space is cheaper than life is long!
Using the NAS in general is no problem. In fact, once iTunes got beyond the initial working out of what needed to be removed from and copied to the iPod, having all my MP3s on the NAS and copying direct to the iPod was no issue.
Following some sage (and frankly scary!) advice at ilounge (http://forums.ilounge.com/showthread.php?t=163611), I've decided to keep two copies of my MP3s. The fact that my fiendish NAS plan has failed is hurting more than the not-all-that-traumatic reality of duplicating 140GB of files if truth be told!

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