Start over? 5th Generation?

I don't know if my ipod is considered "5th Generation." It's a 30GB I bought a couple of years ago, supposedly it has video capability, but I've never used it.
My question is, Can I start over?
I had a PC when I got it and loaded all of my CDs onto my PC and then onto the ipod. I've never purchased anything from itunes. Over the course of the two + years, my ipod has quit playing a lot of the songs on it. When I pull up the library on the PC, many, many, of the songs have "!" next to them and it doesn't tell me what that means. So I deleted and re-ripped those songs. But eventually, more and more songs get the "!" and stop playing. I'd say about half of the songs on my ipod no longer play.
Now I have a mac and I'd like to just wipe my ipod clean, re-rip all of my CDs to my new mac and start all over. I want to make sure all of my songs stay playable on my ipod so I don't have to keep doing this.
1) how can I safely wipe everything clean and reset the ipod so that no trace of whatever problem was causing all of the "!"s remain.
2) What does the "!" mean? How is it fixed?
3) Is there something I can do while re-ripping my CDs to ensure that I'm not doing something to cause all of the "!"s?
Anything else I'm not thinking of?
Thanks!

*1) how can I safely wipe everything clean and reset the ipod so that no trace of whatever problem was causing all of the "!"s remain.*
Restore the iPod in iTunes on your Mac
*2) What does the "!" mean? How is it fixed?*
It means that iTunes cannot locate the original file, it may have been moved or deleted outside of iTunes. If the file is returned to the location it was in originally iTunes will find it: iTunes: Understanding the Symbols Next to Songs
*3) Is there something I can do while re-ripping my CDs to ensure that I'm not doing something to cause all of the "!"s?*
You could set iTunes to copy everything to the iTunes music folder when you add anything to the library: iTunes for Windows - Importing music and video already on your computer
Adding songs from CDs to your library

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My iPod touch 5th generation had white screened an it won't let me rest it by holding down the home button an the power button for ten seconds I've pulled it in to iTunes an its not being detected what can i do as its starting to over heat?

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If you can't get it to shut down or restart when holding down the Home and Sleep/Wake buttons and you can't get it recognized in iTunes to restore it, the iPod may have suffered a hardware failure and will need to go to Apple for service. Someone else here may have additional suggestions, though.
There is no "fifth generation" iPod touch, by the way, just for the sake of clarity; not yet, anyway.
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Hi. I rarely resort to forums like this to fix a problem but I can't seem to find anyone who's had the same issue.
Today I connected my iPod touch 5th generation to my Windows 8.1 PC to sync some songs onto it. I ripped some of them from a CD, others I got from Home Sharing with my brother. I tried to sync 12 songs to my iPod. At first, it looked like 8 of them had synced correctly, not greyed out or empty bubbles. I tried to add the rest and they refused to sync. All the songs from Home Sharing refused to sync to my iPod.
I tried something I normally try after an issue like this occurs - I select all the songs I've downloaded/ripped/gotten from homeshare and right click and select Create MP3 Version. I have my import settings as MP3 because I have other devices that also use my ripped music. I deleted the original versions after the new copies were made and moved them to recycle bin. Deleted the greyed out songs from my iPod and all the ones i'm trying to resync, and put the new versions on. It got stuck on syncing for about 20 minutes, making me late for something so I canceled the sync, ejected it, and unplugged it.
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Try:
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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. Done
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- Reset all settings
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Make an appointment at the Genius Bar of an Apple store..
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Not Charge
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And
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Apple Retail Store - Genius Bar
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Try:
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Click here and follow the instructions.
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Hi
I have a 64GB ipod touch 5th generation ipod touch. It (and itunes) has the latest software.
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Connect the iPod to your computer and look at the storage used by the various categories as shown in the colored bargarph in iTunes.
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To restore to factory settings/new iPod see:
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Start over? 5th Generation?

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