If you truly are playing for the first time, play a couple games with basic to find your racing style and see how often you car is damaged. From there, move on to advanced rules.
My buddies are the opposite, they don't want to street race and they like the basic rules because they can take more risks and go faster without worrying about a particular part of the car. Seems with their mentality, street racing would be more popular. Besides that, I'd say start with any street track that looks the most fun. I am intrigue with the Docks' layout but I have yet to play that one.
Only the advanced rules are needed. I think the best map is race city because it has the most special rules. However, if you just want a simple game then any of the ones without special rules will work better - monaco, sebring, valencia, hockenheim or singapore.
Don't forget to print out the two newest drivers - Pipo and Boris.
I sometimes use the Formula One cars on the street circuits without using the special rules. It's interesting due to thinner roads and land changes. Just disregard any areas where people e.g. shoot at you, or you have to avoid debris. Race City on the original track is an awesome one to do without special rules. Chicago also.