iPod Forum (click on link) is a worthwhile place for both Windows, Mac & Linux users of iPod to check out. There's a forum, freeware available to help you, etc. Check it out! There's also
iTunes forum sections for windows & mac users.
Worth knowing about is
ipod reverse music transfer which is about extracting your songs from iPod back to your or another computer. There's different 3rd party utilities which can do this for mac & windows.
Mac users should see
iTunes & iPod issues for Mac OSX
To copy songs to iPod without iTunes:
Anapod, or
ephPod /
EphPod, or
MediaMonkey & also see
iPod Utilities. WinAmp using
ml iPod plug-in. More can be found at the iPod forum.
For
videos, they need to be either
mpeg 4 or
H.264 format. So probably best to aim to get a hold of those video format files. Mac OSX users who have QuickTime Pro can convert other formats easily to either of these formats. There's now other free programs for OSX users to convert easily (search the apple site.) For windows users, see
Video to iTunes/iPod. One conversion tool for windows users is
3GP & how to use it & also
Videora iPod Converter (free/donateware) & others are in development. Others I've seen are not free & had mixed reports about them. To copy them without iTunes:
Anapod is one. But again, either the iPod/iTunes forum is a good place to search for up-to-date articles about this or the apple forum. More about 'how to use' Videora &
'other' techniques of converting video from different sources to iPod see
HERE (for links). AND
Handbrake (FREE) - MacOSX, Linux & Windows, also
MPEG Streamclip (FREE) - MacOSX & Windows are both great converters. Dual-Pass recommended for better quality for each of these & check the option for iPod conversion on each of these programs.
Apple articles:
(sorry Apple seems to frequently change url location or remove certain help pages) *
iTunes & iPod Discussion forums,
___ *
iPod classic How To's,
___ *
Which Files Work With iPod and iTunes,
____ *
iPod Higher Learning:things you can do with your iPod,
____ *
Can't transfer videos to iPod,
____ *
iPod Features Guide,
____ *
QuickTime Pro: DV format movies may require adjustment for iPod,
____ *
Verifying iTunes video conversion and iPod video syncing using sample QuickTime files,
____ *
Adding, Browsing, and watching videos in iTunes,
____ *
iSquint (freeware) conversion tool for - iPod + iTunes (Mac OSX only),
____ Other utilities search,
____ Other utilities search 2 * Audio & video formats supported on iPod. * iPod
Updates for specific models.
_ iPod issues? The 5 Rs (Reset, Retry, Restart, Reinstall, Restore) Video specifications for iPod: Video
H.264 video, up to 1.5 Mbps, 640 by 480 pixels, 30 frames per second, Low-Complexity version of the H.264 Baseline Profile with AAC-LC audio up to 160 Kbps, 48kHz, stereo audio in .m4v, .mp4, and .mov file formats; H.264 video, up to 2.5 Mbps, 640 by 480 pixels, 30 frames per second, Baseline Profile up to Level 3.0 with AAC-LC audio up to 160 Kbps, 48kHz, stereo audio in .m4v, .mp4, and .mov file formats; OR
MPEG-4 video, up to 2.5 Mbps, 640 by 480 pixels, 30 frames per second, Simple Profile with AAC-LC audio up to 160 Kbps, 48kHz, stereo audio in .m4v, .mp4, and .mov file formats
_____ (iTunes is a little less fussy but almost the same)
Converting video to iPod format using QuickTime Pro (Mac OSX instructions):
Converting videos using QuickTime Pro for use on iPod/iTunes
ucats it sounds like you need to manually add & remove songs from your iPod.
'Manually Manage Songs & Playlists.' Did you see the
iPod Tutorial I think Lessons 4 & 6 might help you to understand how to overcome your issue. I would recommend EVERYBODY use the manually add & remove songs from their iPod. (Sample image bottom of next page.
Manual settings for iPod) No complications then.

Tutorial lesson for this is
HERE & play the video tutorial to let it show you & click Learn More for more details.
It seems the apple tutorial page has been changed, as have location of some of their other document pages. So I'll add some details here. How to
Manually add songs to iPod:
To manually add to your iPod:
1. Make sure that "Manually manage music" is selected.
2. Click Music (below Library, on the left side of the iTunes window) and then drag songs and playlists to your iPod.
QuickTime video tutorials: _ 1.
Manual Updating of iPod,
_____ 2.
Update selected playlists only to iPod _____3.
Add/Play video on iPod/iTunes,
_____ 4.
Transfer iTunes Library via iPod How to Share your iTunes songs: _ 1.
artist & album organisation ___ 2.
How to Share Folders (click on link) Manual updating iPod.mov ______ Update selected playlists only.mov * Warning 'some' of the above QuickTime videos are encoded using H.264 or 3ivx with AAC audio. If you are having problems watching any of them, then use this player: VLC - (click on link) _ (choose nearest mirror site). .