Ipod skips 4-5 random songs after each sync

I bought my first ipod last thursday and i have had numerous problems starting from the moment itunes attempted to import my existing music library. I have fixed most of the problems myself, but there still two that have me stumped.
1) After i sync my ipod, there always seems to be a handful of songs that when they come up in a playlist, my ipod will wait a few seconds before skipping the song without playing. I say the songs are random because after i sync it again, the songs that wouldn't play before will work, but a different couple of songs (that worked before) won't play and get skipped. Yes, i already tried the 5 R's and the problem persists.
2) Twice now, after i pause my ipod and press play again after a few minutes, it will refuse to play any songs at all. It will just skip through them all, much like the first problem. I can get it to play songs again with a reset, but if its going to do this twice a week, i need to find a more permanent solution.
I did restore my ipod last night and problem #1 still occurred. I have no idea yet about #2, but if anyone else has experienced these problems, help would be extremely appreciated!!

Anyone want to help at all? This is getting a little ridiculous. Honestly, with all the problems I've been having, especially with itunes, I really don't think I'm ever going to buy an apple product again.

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Next, reset your iPod. If the music is still skipping then the fastest fix is to use your restore/upgrade software to restore the iPod. This will erase the music and re-install the iPod's operating system which will take care of possible problems 2 and 3.
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Try:
- Reset the iOS device. Nothing will be lost
Reset iOS device: Hold down the On/Off button and the Home button at the same time for at
least ten seconds, until the Apple logo appears.
- Unsync all music and resync
- Reset all settings
Go to Settings > General > Reset and tap Reset All Settings.
All your preferences and settings are reset. Information (such as contacts and calendars) and media (such as songs and videos) aren’t affected.
- Restore from backup. See:
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Good luck!
Occam's Razor nearly always applies when troubleshooting technology issues!
If anyone has been helpful to you, please show your appreciation by clicking the button inside of their post. Please click here and read, along with the threads to which it links, for helpful information to guide you as you proceed. I always recommend that you treat your BlackBerry like any other computing device, including using a regular backup schedule...click here for an article with instructions.
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IPOD Skipping to a random part of songs

Hi people,
I have a 5th generation iPod. Recently since installing the latest patch 1.2.1 I've noticed from time to time, my iPOD while playing a playlist, after completing a song will start the next song, (duh wait for for the problem ) but not from the start of it.
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Hello,
Everytime when I add new music to my playlist on my ipod nano, I disconnect and go back to continue to play same song on where i left off, it randomly goes to a new song after syncing?! I always keep my playlist on shuffle, could that be the problem? It does not happen to my podcasts, which continue on where i left off whenever I sync. I'm confused, please help

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Try resetting your iPod...
Resetting iPod
If that doesn't work, make sure your iPod's software is up to date...
iTunes
iPod Updater
Updating iPod's Software
If you updated and the problem persists, try a restore...
Restore the iPod
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Troubleshooting Songs That Skip On iPod
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i have an ipod touch 4g as a gift recently. i downloaded the newest version of itunes from the internet. i transferred my songs from my computer to itunes music library. when i sync-ed my ipod touch to my itunes library, it doesn't show Any of my songs that i have in my itunes music library. None of my songs are listed on my ipod touch under "music," whether it be "recently added" or any of the other categories.
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Ipod skips 4-5 random songs after each sync

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