Videos not playing or syncing

I bought some videos through the iTunes store using iTunes 7.1.1. For awhile they all played in iTunes and synced fine to my video iPod, but then I upgraded my OS to 10.4.9. This caused all sorts of problems with my network (printing, sharing, etc.) so I reinstalled Tiger and am now again running 10.4.6. Music purchased before and after the upgrade/downgrade plays and syncs fine, but none of the videos I've purchased will play in iTunes or on the iPod. They show up in the iTunes library, but not on the iPod.
I'm guessing there some sort of sweet spot of OS/iTunes versions that's causing this, but can't find and related threads to figure it out. Anyone have any thoughts as to what's going on?
I have not tried any non-iTunes videos.
Thanks!

Anyone?? Please help!

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Complete name                            : E:\DCIM\136_0317\MVI_0084.MP4
Format                                   : MPEG-4
Format profile                           : Base Media / Version 2
Codec ID                                 : mp42
File size                                : 2.27 GiB
Duration                                 : 9mn 15s
Overall bit rate                         : 35.1 Mbps
Encoded date                             : UTC 2014-03-17 18:44:17
Tagged date                              : UTC 2014-03-17 18:44:17
Video
ID                                       : 1
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Codec ID/Info                            : Advanced Video Coding
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Bit rate                                 : 34.9 Mbps
Width                                    : 1 920 pixels
Height                                   : 1 080 pixels
Display aspect ratio                     : 16:9
Frame rate mode                          : Constant
Frame rate                               : 59.940 fps
Color space                              : YUV
Chroma subsampling                       : 4:2:0
Bit depth                                : 8 bits
Scan type                                : Progressive
Bits/(Pixel*Frame)                       : 0.281
Stream size                              : 2.25 GiB (99%)
Language                                 : English
Encoded date                             : UTC 2014-03-17 18:44:17
Tagged date                              : UTC 2014-03-17 18:44:17
Color primaries                          : BT.709
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Audio
ID                                       : 2
Format                                   : AAC
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Bit rate mode                            : Constant
Bit rate                                 : 256 Kbps
Channel(s)                               : 2 channels
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Sampling rate                            : 48.0 KHz
Compression mode                         : Lossy
Stream size                              : 16.9 MiB (1%)
Language                                 : English
Encoded date                             : UTC 2014-03-17 18:44:17
Tagged date                              : UTC 2014-03-17 18:44:17
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