Hell man, I do think if DC is going keep Dick tied to Bruce's apron strings they might as well double down on it and go all in. Really make it work for him, right?
I like the Amusement Mile idea too.
Good points on Conner. He's definitely better paired with Tim than sidekicking for Dick.
As for Jon, it'd be great to have Dick train him. It makes perfect sense too, though it might pull Jon away from Damian, which would be regrettable for both characters. As for Jon, he's generally a really good kid; optimistic and fairly happy, quite smart. But he's also got a very healthy dose of Lois Lane in him and can be sneaky and cunning. He's got his father's temper. He's got the Superman power set but isn't nearly as powerful as his father, but everything points to him possibly becoming even more powerful than Clark once Jon grows up. He hasn't met Dick yet, as far as I know, but they'd get along so well it'd make Damian physically sick.