What are you using to rip the movie to your HDD? How big is your original file and are you removing foriegn audio and subtitle tracks? Full disc or movie only?
If you are using DVD Shrink to rip then it probably isn't cutting it. I would suggest DVDFab HD Decrypter (free @ http://www.dvdidle.com/free.htm ) and then go straight to DVD2One. This should also save you a step because DVD Shrink and DVD2One basically do the same thing (compress), but IMHO DVD2One does it slightly better. Once you have successfully "backed up" your title you can burn with Imgburn or your favorite burn engine.
you compress it to a folder, ignoring the warning that the size will be too large for a DVD. You then compress the compressed image again . . .
Personally, I used AnyDVD and ICOPYDVDs2. They handled backing up my copy of "The Condemned" quite nicely . . I watched it on a 32" Tv and it looked very good
I'm not sure how much it is . . . I received it with a DVD burner that I purchased at a computer show years ago . . . You can get a 30 day free trial here: http://www.brothersoft.com/dvd_video/dvd_copy_software/icopydvds2_30_day_trial_45525.html There's several editions available . . mine is the Standard Edition Victor