Playing inside your comfort zone is fine as long as you're not getting stuck in bad habits. I'm really happy y'all are having fun on the Streets! Do we have a club yet? Is it already full? Don't be too scared to hop online. You WILL find people at or below your skill level. And don't worry about the other player's time! If they don't want to rematch they don't have to!
I don't gatekeep in either direction: classic controls are better if you want full control of your character, but modern is totally viable. I'm not sure I like that it's not transitional (it doesn't teach you how to play classic) but if you are comfortable with those restrictions, it's FINE!
But also: don't be too scared of classic inputs. They're not as hard as they seem.
World Tour = Streetmue. Learning some of the game first is a good call! World Tour has tutorialization, but you also run the risk of learning bad habits because you spend a lot of the game without a full toolkit.
Bogard's comments