I can answer at least half of that question for you, and I am sure there are others who can answer the rest.
Yes, you will have to get the Mobile option to convert to your iPods. That's not supported in the free version (DVDFab HD Decrypter) or the trial version of Platinum or Gold (as far as I remember... it's been awhile).
Multi user licences are available, and if someone here can't help you, try emailing firstname.lastname@example.org, and explain what you need. I'm sure they'll prove helpful.