The loud approach is the more difficult as some of your hacked time is taken up with crowd control. The smart approach lets you steal jewelry uninterrupted making the mission easier to complete.
The more expensive driver will give you directions and select bikes suited to the course. But the cheaper driver does his job. Stay behind the other crew to let you know where you are going and the road bikes don’t handle too bad in the mud.
If you choose the cheap gunman he will crash his bike and you will loose a substantial part of the money.
Depending on which hacker you choose you will have different amounts of time. I found that Christian Felts gave me just enough time to take all the jewelry.