google map buddy sounds nice,
but if you want to make a quality map, I dont know of any software where you dont have to draw/trace everything and god help you if you want to add contours lol
Roads/streets - if you make the roadline say 3mm, clone the line and make the top line thinner, say 2mm. With lower line black, the upper white, you have an 'outlined' road - gets tricky at junctions so move the white lines into a higher layer so as they always show over the black (using any vector drawing programme)