Personally I would do whatever I could to keep the driveway flat. There's nothing like a flat driveway! With adequate runoff of course. However, at the street you don't want the approach so steep you can't get a lowered Camaro in there without dragging the headers! If it works out to raise the drive, the approach is doable, and the front yard just needs more fill to bring it up....well you know what I would do!
