GLF - A few answers / my opinions:

Here is the map I use... a bit outdated but still quite useful: http://media.tripod.lycos.com/2567851/1586661.pdf

Captaind's son Linston is a great driver that could probably hook you up with a great day in the country: http://redplate-negril.com/ 876.376.3652

As you mentioned, one man's sketchy is another man's calm... that being said, I typically feel fine walking on the road at night.