Video encoding

Ok so recently I've been looking to backup my dvd collection to make it more accessible since I'm using media center with Windows 7.

My question is ISO vs handbrake x.264.

I had heard x.264s quality was supposed to be on par with the original quality, but it took time to encode. Ok, I'm fine with that. So I used handbrake and encoded at the ps3 default setting, which gave 2500kbps. I played it and it looked ok, but not great. So I made an iso rip and compared the two's quality. The DVD rip looked much better.

Am I doing something wrong or did I have my hopes set to high for x.264?

I have just been doing tests for now to decide what method I want to commit to. I have a little over 100 movies and would like for them to be encoded uniformly, that's just my minor ocd. Also, I've noticed that my rips don't have any information with them such as cover art and the such as they do when they are recorded from DirecTV. How do I get this info added to the files?