DO This
I did this for some and they worked fine
It's from the first post on that other thread:
https://forums.macrumors.com/threads/437954/
cowm007 is credited for figuring this out and sharing with us.
Open Handbreak
Open Source > VIDEO_TS folder you want to convert on Hard Drive (if pre-ripped) or on actual DVD.
Once Handbreak scans the VIDEO_TS and finds the Main Title it will give you the length and # of chapters.
Then select the iPhone preset in the right hand toggle area. This will reduce the bitrate to 960 and shrink the dimensions of the output file. Default Format will be mp4 and default codec will be AVC/H.264/AAC Audio. FPS will be same as source also.
Here is what you want to do:
Change Average Bitrate to 2000-2500 (kbps) I haven't tried more than 2500 but it might be fine?
In the Codecs drop down menu, choose AVC/H.264/ACC+AC3 Audio
Then click on picture settings:
If this DVD films (not TV, you can tell by the FPS, Film=23.98xxxxxx) then the only thing you want to change is where it says Anamorphic and there is a drop down menu. Change this to Loose or Strict and you will see the preview image enlarge and the output dimensions increase. If you are doing Films then this is the only thing you change on this screen. Then hit Close.
When you changed the codecs, Handbreak already finds the AC3 file and will also convert a copy to stereo AAC.
With most movies you are ready to roll now.
Sometimes I double check the Audio/Subtitles tab to make sure it pics the right AC3 track, especially if I am ripping straight from DVD. Most region 1 DVDs, USA + Canada DVDs set the default audio to English and Handbreak knows this. Also you can boost the bitrate of the AAC Stereo track to 160 kbps from 128 kbps if you want.
Assuming that you are an English speaker, if your film is in English but has English subtitles for when foreigners are speaking (like Behind Enemy Lines) then you should check Forced Subtitles Only. This will only put the subtitles ON just when the the actors are speaking another language.
I have done this for many movies, and they play fine on my iPhone, AppleTV, Quicktime, Frontrow, and VLC. Some of these have been pretty big like Lord of the Rings Triology (close to 4 GB) but most are 2-3 GB. I am not sure if this will work for the 5.5G iPod but you should try one and post back on this thread or the other one.
I hope that these are decent step-by-step directions.
Good Luck