Is there a "replace files" bug in iTunes? Plays fine in iTunes- not on Pod

Hello, all. Long story short, I'm re-ripping all my CDs at a higher bit rate. I'm going from 128 Kbps AAC to 192 Kbps AAC (variable bit rate.) Now I'm having issues.
So far, when iTunes asks me if I want to replace my existing files before I rip, I say "yes," but now I'm wondering if that's a big mistake due to a bug in iTunes. Why? Well, although the newly ripped album plays fine in iTunes and through my iPod (using it as a hard drive through the computer), once I disconnect my iPod and make it portable, the iPod will skip track #2 (for example) of a 9 track cd.
I've reset my iPod - no change.
I've deleted the album from my iPod and dragged it back on there - no change.
I'm trying to track down the root of the problem. The replacement file is obviously fine, and even plays in another media player. Someone said "replacing" files is bad because iTunes doesn't replace gapless playback information, and it uses old data for your newly sized files. Is that the root of my problem? Does iTunes have a "replace existing files" bug? It's the only thing I can think of. A solution would be to have iTunes re-analyze all my iTunes tracks for gapless playback and other data, but that doesn't seem to be an iTunes option. Any ideas? Re-ripping the cd is not an option. (But for all you whistle blowers, rest assured it was a cd I bought, so everything is legal.)
5th gen iPod with video Windows XP iTunes 7.1.1.5

Have you updated your iPod and iTunes sofware?
most cases, iTunes can play these high quality songs, which is meant for newer mobile devices like iPhones, iPod Touch, nano and iPad, which the older iPod cant play, but only playable with iPod classic sofware version 2.0.4
most likely it is an incompatible song format, read this Apple support article.
http://support.apple.com/kb/HT1334?viewlocale=en_USet
If your iPod software is version 1.1.2, then you have to use lower quality format.
Can you select the problematic song, and Advance -> create iPod version

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Try this Hard Reset
After charging till full charge, at least 2 hours (preferably 4 hours)
Toggle the Hold switch, make sure you dont see the red mark when you do the next step
Reset the iPod -> Press Menu and Center button simultaneously for about 10 secs till the Apple Logo comes ON
Then release the buttons
Select your preferred language.
Test the sound again.
Here is the Apple support Article on the 5Rs
http://www.apple.com/support/ipod/five_rs/classic/
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Hi.
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Hope someone can come up with an answer or Apple puts in fix.
For now I set iTunes to be the default program to open for this file type but would it rather have remained Quicktime.
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Format                           : Wave
File size                        : 36.8 MiB
Duration                         : 1mn 49s
Overall bit rate                 : 2 822 Kbps
Audio
ID                               : 0
Format                           : PCM
Codec ID                         : 1
Codec ID/Hint                    : Microsoft
Duration                         : 1mn 49s
Bit rate                         : 2 822 Kbps
Channel(s)                       : 2 channels
Sampling rate                    : 44.1 KHz
Resolution                       : 32 bits
Stream size                      : 36.8 MiB (100%)
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Try deleting them from the iPod and redownloading them directly to the iPod
Downloading past purchases from the App Store, iBookstore, and iTunes Store
Next:
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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.
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Garageband output on BT speaker? Too much latency, but iTunes plays fine

Hi all
I have a Creative D200 that I like to use to play iTunes music in my office.
Today I tought that I would like to play my electric guitar, since I am basically alone and can make as much noise I want (yay).
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Hi Becca_hague,
Thanks for the post.
You will need at least 2MB to effectively run BT Vision. The real problem here is not your speed, its your connection constantly dropping out. If we can figure out why your connection is dropping and fix this, then your speed should recover by itself.
Your noise margin is not very high at all which is strange, as one of the main culprits of a dropping connection is noise interference. The fact you are already in the test socket rules out internal issues. It may well be that the router you are using is faulty. On the other hand this may not be the case.
I would like to run a few checks on the network side of things, to see if anything stands out as odd. Please drop me an email to the email address in my profile. (click on my name and you will find the address under the "about me" section). Include your BT account details and the link to this thread.
Cheers
Sean
BTCare Community Manager
If we have asked you to email us with your details, please make sure you are logged in to the forum, otherwise you will not be able to see our ‘Contact Us’ link within our profiles.
We are sorry that we are unable to deal with service/account queries via the private message(PM) function so please don't PM your account info, we need to deal with this via our email account :-)

Song corrupted in iPod while plays fine in iTunes, but can't be re-imported

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I can assure you the song is fine (the ine in my PC), compatible with iPod (mp3, part of a group that all work), not such thing as read-only etc. What's going on and how do I fix this?

Other similar cases:
https://discussions.apple.com/message/2864108#2864108 (very old post, has comments, but no help from Apple)
https://discussions.apple.com/message/11487143#11487143 (recent post, has no comment)

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I've tried deleting the song from the iPod and restoring it by deleting it from my iTunes, updating the iPod, then restoring it to my iTunes library and updating the iPod again.
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See if these help.
iPod does not play content purchased from the iTMS.
About Authorization and Deauthorization.
Authorization FAQ.
Troubleshooting songs and audiobooks that won't play on the iPod.

Is there a "replace files" bug in iTunes? Plays fine in iTunes- not on Pod

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