How to convert a DVD to iPod format
1. You will need to download DVD Decrypter from here http://www.dvddecrypter.org.uk/. Install it and open it up. Now put your DVD into the DVD drive.
2.
On DVD decrypter go to Mode and then select the IFO option
3.
Then go to tools then settings and then go to the IFO tab, then
under Options, change File Splitting to None and press OK. 
4.
Go to the main screen and click the Stream Processing tab. Enable it and
only select the first video listed. Note that home encoded movies do not
support subtitles of any kind and that your file can only have one type of
audio. 

5. Before you begin ripping your video, note the destination of the video file. This is where your raw DVD rip is going to go and it will be rather large in size. If you want to change the directory that DVD Decrypter will output to, click on the Browse button and navigate to the folder you want and press OK.
6.
Now that you know where the movie file is going,
click on the Decrypt button to start decrypting the DVD to your hard drive.
Once it is done, close DVD Decrypter. Expect a 4 GB to 6 GB movie to take about
12 to 18 minutes. 
7. Now you are ready to convert your files. There are various different free programs to convert videos to iPod videos around. But I would recommend Jodix Free Ipod Video Converter which you can download from http://www.ipod-video-converter.org. Install it and load it up.
8. Now click Add Files and locate the file you decrypted on DVD decrypter early and select it.
9.
Once you have added your file it will pop up
with a wizard to guide you through the
proceedings. You can change quality,
resolution, etc. 
10. It is also possible to change the ID3 details (Video name, author, genre, etc) though it will take all it can from the file itself. You don’t really need to worry about that because you can change it in iTunes.
11.
Now click the Start button, a progress screen
will pop up like below. 
12. When it finishes you should get a message like below. Click Yes then open iTunes and drag the file it has created and drop it into iTunes.

Other information
To convert files from Youtube to iPod go you vixy.net and type in the url of the Youtube video and select into format ‘MP4 for iPod’. It will then convert the video to iPod format online and you will be able to download it and drag it into your iTunes library.
Another good program for converting files which I believe some will find slightly more complicated and I believe is less stable is Videora iPod video converter. Go to http://www.videora.com/en-us/Converter/iPod/.
Expect conversions on all free software to be exactly or maybe slightly faster than real-time. So a two hour movie would probably take two hours to convert after it has been decrypted so in total the whole thing might take three hours at worst. But it all depends on your computer. If you are prepared to pay some companies claim to provide very fast conversions.