As someone who is going through this process right now, it takes more effort than might be expected. I've got a small-to-mid size library of about 200 movies and about 60 seasons worth of TV shows. Both my Macs have been encoding 24 hours a day for the past five days and I'm about half way through my movies.
My suggestion is to do it right the first time. Take the time to research quality settings, make sure you pay attention to some of the smaller details (i.e. which movies have subtitles that you need to double-check are being encoded), and tag every field correctly. This should save you a lot of time in the future.
Another suggestion I have is using Handbrake's new Apple Universal preset. You might not have an iPhone/iPod or an AppleTV currently, but don't discount the possibility that you'll be getting one in the future and would like to play videos on it. The only things that sucks more than encoding all your DVDs once is encoding them twice.
Also, don't underestimate the amount of time it takes you to get everything in order. I've got both my computers running 24 hours a day, but I still have to make sure I've got enough movies queued up to keep it running, plus tagging the video files sometimes takes quite a while. I've noticed I'm spending two to three hours a night getting everything looking good in iTunes and making sure that everything is ready for the next day of encoding.
Finally, make sure you've got the storage space. The DVD files ripped straight from the disc can add up quickly on your internal hard drive. So even if you have an external hard drive that you're planning on putting all these videos on, you've still got to make sure you leave yourself enough space on your internal hard drive to do the actual encoding. Make sure you're deleting the VOB files as soon as you're finished encoding the movie; they take up quite a bit of space.
Obviously, I think all of this is worth it to ensure that I have video files that look good and play on all my devices, but it's not as simple as it often sounds.