Dont know if this will help you or not, but I put my DVD movies on my Windows Media player on my PC. Then I drag it to the Roxio Manger that's in the BB Desktop manager. I sync my phone and it automaticlly transfers it to my Video files in my BB. It does take ALOT of memory though. Hoepfully this helps, if not I'm sorry.
I use SlySoft's AnyDVD and CloneDVD Mobile to convert to ipod format but they do have a BlackBerry option that I haven't tried yet. AnyDVD is for stripping the CSS protection so CloneDVD Mobile can do the conversion. If you bypass CSS some other way you won't need AnyDVD.
Neither are free but have trial periods where everything is fully-functional, so you can see if they work for you.
Posted from my CrackBerry at wapforums.crackberry.com