here
https://www.mapillary.com/app/?pKey=353216442838770&lat=32.7554912&lng=-17.1483521&z=17 it is where the road changes from asphalt to cobblestone.
I would suggest for the first part smoothness="excellent" as i have changed it. The following (cobblestone)part is in good shape, but "excellent" does not fit imho (roller skates?). But feel free to change it to the appropriate smoothness you think it might more accurate.
I have used the street during my visit of Madeira.
I have changed most of the estrada Doutor R.Monteiro from "bad" to "excellent"(!), it seems to be renewed in the last time. Only the last part you have mentioned is not renewed. It is build with cobblestone. So i changed this part again back to "bad".