I actually came to like the Tim Drake Robin on the later animated Batman, and the strained relationship Batman had with Grayson. 'Old Wounds' was a great episode and dealt with some legitimate issues. So did 'Over The Edge' and the Beyond 'Return Of The Joker'.
I also like the usage of the much younger Drake Robin as it puts more of an emphasis of responsibility on Batman, and challenges that because Drake is so young. I guess as we get older and either have kids of our own or friends with kids, it hits home more. Like if I knew a Batman or whoever who was doing the same, regardless of how 'good' their reasoning would be, I'd tell them it's wrong to put someone so young into those kinds of situations. So I think it makes us question our moral stance on Batman, maybe more than anything...as we easily support his spying, his excessive force, the collateral damage, etc. In a lot of ways it's a gut-check to the escapism from an adult's perspective....and to some degree, Batman in unhealthily compensating for the trauma he suffered as a child by projecting his current strength and power onto another's. A highschool-to-college aged Grayson is one thing (even if he started off younger)...a 12-14-ish Drake is another entirely. And that's why I like the Drake version more because I think it's more morally challenging.