IF you feel adventurous
If any only if you feel like trying a grand experiment (nothing harmful, just complicated till you do it once), try
THIS. They're automator (think script) functions that control ripping and converting of DVDs to avoid user interaction.
I've been using them to bulk-convert my DVD library. Once the initial setup is done (~20 minutes to install all the software), you just insert a DVD. The script will detect this, and ask whether it's a TV show or a Movie. You'll then be asked the title (95% of the time, this will be prefilled from the DVD volume name, but not always), and then it will rip the disk to your hard drive.
Then later, and you can have ripped anywhere from 1-100 disks to your drive, you start another automator function that uses the command-line version of Handbrake (no user input necessary for this, and it's faster than the GUI) to convert the ripped disks to a format that iTunes/iOS likes. (h264 MKVs). Also supports BlueRay burning if you want to make this a substantial investment, but I'd start small
The end result to this are MKV video files that are a very reasonable size (~1.2GB if SD, ~1.7 if HD) that include subtitles, iTunes tags, as well as poster art for the Cover Flow file browser.
I'd be happy to help you implement this (I can Teamviewer into your machine to help you setup). No other reason than it's an excellent solution that will help you to convert your life away from physical media. (No charge lol). After the initial setup is done for the scripts (majority of it is just downloading the needed 'helper' applications), it's simple and quick. <<That offer is open to anyone, btw.