I download vimeo videos and put them on my ipod frequently. Here is how to do it using a Mac and Safari.
First, go to the vimeo page and let the video load completely. Now you have one of two options*, what I usually do is go to Window (in the toolbar) and then click on Activity then in the new window that opens double click on the file that is the largest size (Vimeo videos, depending on their length, will usually be around 30 MB). Once you do so it will download the video in .flv format to your dekstop.
From here go to this new site called google.com and download a program called iSquint. Once iSquint is installed open it and drag the .flv video from your desktop into iSquint and that will convert it for your iPod.
*I prefer to download the .flv file from Vimeo because it is smaller and the source video (which only vimeo lets you download, not youtube or facebook) is often a pretty large file that will not only take longer to download but also to convert in iSquint.
If you any questions, just ask. It's really not as confusing as I made it sound and once you do it a couple times it is super easy and you'll crank out videos to your iPod in minutes. Traveling circus installments are great for those 1.5 hour lectures.