While some of the women admittedly looked a little too pixie like, in an odd way I think it suited Barbara at least. There's something about the old design that made her look a little to young for me, though that might have as much to do with the original voice actress too.
We saw in B:TAS that Babs was in college alongside Dick, and she seems to have been a year or two behind him, since she wasn't graduating along with him in TNBA's "Old Wounds" flashbacks. So she was probably 18-19 in B:TAS and a few years older in TNBA. (The odd thing is that Mystery of the Batwoman
has her away at college and treats that like a recent development. I figure that was grad school.)
As for the Riddler, I think he's an almost impossible character to write for. Nobody can ever seam to decide if he's a vanilla Joker of a campy Luthor. Personally I've always thought he should be played as something closer to The Question (and not just because of the ? fixation.) That is a fierce intelligence but misunderstood and a notch or two past that old genius/madness line.
Well, that's kind of the way he was played in B:TAS. He wasn't Joker-like at all, but a smart, calculating, debonair figure who prided himself on his intellectual superiority. Unfortunately, the first couple of Riddler episodes were undermined by seriously lame riddles and an overdependence on computer-game plot gimmicks. The only one that really depicted him credibly as a shrewd intellect was "Riddler's Reform."
The version of the Riddler in The Batman
was actually more effective. He was seriously creepy and cold there, effectively played by Robert Englund, and in the show's fourth season, TNBA veteran Stan Berkowitz gave him a tragic origin story that felt more B:TAS-like than the B:TAS Riddler's rather pedestrian origin.
As for Oswald, it wasn't just his character design. I liked that they made him a semi-legit businessman, somewhat filling the void left by all the old mob bosses. A more stable presence that Batman can intentionally keep in place to block anyone more dangerous muscling in.
Yeah, the Iceberg Lounge was an interesting new twist. I like it that Dini has introduced it in the Batman comics he's writing these days. Although he's working in the main DC universe now, his Batman comics almost feel like they could be in the B:TAS continuity (but with more overt violence). Actually, in Dini's comics, both Penguin and Riddler have gone nominally straight, with Riddler hiring himself out as a consulting detective. They're both still kind of disreputable businessmen, but actually staying within the law, unlike TNBA's Penguin, who was still a gangster using his legitimate business as a front.
Actually, though, my problem with B:TAS was that there were too many mob bosses. Aside from Thorne, the only one we saw more than once was Stromwell, and that was only twice. Otherwise, new mob bosses kept coming out of the woodwork and disappearing again. Particularly in Mask of the Phantasm
, where we were introduced to at least three major mob bosses we'd never heard of before but who'd supposedly been around for decades. One of them even had a line about how Batman had never leaned on them before, which is hard to reconcile with his approach toward mobsters in the show. It would've been nice to have more continuity there.