There's a residential dead end neighborhood that has a stop sign that I plan on rolling through.
Why would you roll through the stop sign?
To see if I can get away with it.
It's good to always obey traffic laws, as it prevents tickets and accidents. Getting lax about such things will result in you developing bad habits. You should always drive as if you need to be lawful and it will give you peace of mind while driving.
Yeah, I have enough money to pay the tickets so I don't care about those.
Having the money to pay for the tickets doesn't mean that you shouldn't obey the laws of the road. You don't want to waste money, nor do you want to put the safety of others and yourself in jeopardy.