I always saw Rudy as more pitiable than empathetic- so disconnected (by choice) from reality that some basic human decency has left him. He recognizes this, and it is why he is able to avoid the adage "youth is wasted on the young" in his reincarnation. If his previous life were fulfilling and he had no regrets, there would be no drive to succeed 'this time', which is the main crux of the story.

But yes, he's still quite the little perv. You can take the otaku out of Japan...