I have many clients who stress concern about the road conditions in Jamaica.
I just returned from a two week trip to Jamaica and I rode nearly every road from Montego Bay to go Ocho Rios, back to Montego Bay, onto Negril and then back to Montego Bay again. I found the roads to be well-paved and much of the scenery to be very pleasant as you can see in the pictures below.
You pass many scenic vistas, pass by local Schools and churches, as well as small Parrish centres.
Many resorts include complimentary transportation and often the driver will stop midway to your destination so you can grab a cold beer and try some local jerk chicken. Or if you prefer to be a VIP, you can get a private transfer in a luxury sedan equipped with cold beverages and snacks. I had the privilege of enjoying this on my arrival into Jamaica on the drive from Montego Bay to Ocho Rios.
If you are staying in Whitehouse, the roads are a bit precarious, but the drivers are very skilled and knowledgeable.
Overall I believe the roads in Jamaica are very well suited for tourists and the shuttle and private drivers are very skilled at getting you to your destination.