Harry is someone that already exists and has relationships in the world, usually those sorts or RPGs don’t let you customize much. It’s like Geralt or Link. But you do get to develop your personality more through dialogue.

As for the tie skill check, the rest of the game is better about saving skill checks for more difficult tasks. It’s just there at the start to reinforce how much of a mess your character is. You can come back later when the negative modifiers clear and it’s easier.