So I successfully converted one of our DVD's onto our mac and into iTunes, now it's saying I can't transfer because it "won't play on this iPod" ?? Why not??
As you have managed to get it into iTunes, you are almost there.
Right click on the film in iTunes and select "Create iPod or iPhone Version" from the list. You will get a second version of the film in your list that can be copied.
Did you use the free Handbreak tool to rip the DVD? It has built-in presets so that the copy you make should work well with whatever device you picked.