(1) I had no idea that Tim playing DnD was canonical! That’s so great! Here are my brief class ideas just based on archetypes and characteristics! Bruce - Paladin - sacred oath + strict morality; Dick - Bard - Dick is a performer. Plus the comic where he reenacts Cinderella to Class makes me think he’s a good storyteller; Jason - Wizard - reads, studies, and shoots things (with magic);
(2) Damian - Ranger - In tune with nature (or in his case, animals), but also has a focus on physical combat whether it be hand to hand or ranged; Steph - Sorcerer - Sorcerers, like Steph, seem to be charismatic and have a lot of willpower; Cass - Monk - expert at hand to hand combat + her observational skills make sense for an ability focus on wisdom; Alfred - Cleric - support for the more combat oriented players
These are all very good for if I did something like Cycle of the Five Lions, where the Batfam was translated to a DnD-style fantasy world as themselves. Except that Bruce would be an oath of vengeance pally, I think, and it might have to be to Pathfinder world so Jason can be a gunslinger. Wizard also works for him, though. Lots of good ranged attacks.
Damian as a ranger, yes, that’s the first one that occurred to me. Imagine Damian with a bear companion. (Tim: But you know the animal companion isn’t really that useful at higher levels… Damian: I want to ride into BATTLE on a BEAR. Give me that, DRAKE.) And he would do the dual-wield blades instead of being an archer ranger, and they would be katanas.
But gosh, Steph as a sorcerer? PERFECT. All of that wild talent just bursting out. Dick is definitely a bard, very flashy, charisma-based, all about the show. There actually is a ninja class that would work for Cass in some systems, but monk is also good. Alfred as the cleric YES, obviously, but sometimes he gets grumpy and refuses to heal them until they stop being dumbasses for five minutes.