It's up to the POCO. Here they won't allow the eight foot riser if it's more than 3 feet from the edge because they don't allow the line crews to use a ladder on the roof for safety reasons. So they specify five feet, no matter how much of the drop extends over the roof.
If this drop is not going to the building in question I think 230.24 says it has to be 8 feet above the roof, out to a distance of 3 feet from the roof's edge. The exception (4) is for the final span of the drop that connects to the riser on the building served
Somehow the "before" and "after shots got reversed . I hate it when that happens! I will admit that 230 also references the pitch of the roof; this roof is right on the line, and I let the inspector decide. Part of this was based upon the heigth of the riser on the building getting new service; see photos added to "flagpoles" in "photos submitted for discussion."