HA! The best way to start on the street is with a CHEAP, USED 250-600 bike. Did I mention CHEAP? Because you will want to sell it in a year after you buy it new. Believe me, I know, been there many times.
But, you should fully explore all you can with a little engine on the street so that you don't get lured into trouble by a superbike at first. Just try to save money and don't (it's very hard not to) fall in love with your first bike and overspend on it. With that said, good luck on the purchase and DEFINATELY START riding on the street...it is awesome!
Remember, the defensive approach will bring you more joy in the long run because you will not get hurt. Be a wimp, don't pass and get the SKILLS up real good. Then, buy a superbike and pass everything in site........(when safe)