Have driven for years and stayed at many properties, I can not remember ever having one w/o parking. Most are gated and secured at night (some also during the day), if you are an early riser you may have to track security down to get out. I also get night securities cell# if we might be coming in late, we give them a call as we roll up Norman Manley and they will usualley be at the gate to let us in.
Shade is good, but remember coconut tree or breadfruit tree shade when fruit is ripe can wreak havoc on windshield, hoods and roofs.
Most car parks are pretty tight fits. Be considerate and leave room for other cars. Most car damage is "backing into" accidents, I work out the best in and out system that minimizes risk and follow it all week.
I love going to a car wash, but the gardener at the property will usualley offer to wash the car. Just like when I dock a boat I clean the empties out everytime we roll back into the property, the properties trash bins are usualley around the car park and gardener or security will gladly take returnable bottles.
Just me but I use the vehicle multiple times in Negril every day, store runs, lunch & dinner at the place of our choice not limited by location, change money, fruit and veggies, let Coleen walk up the beach I pick her up and run her back, a run up West End just for a change and quite honestly I love to just roll around and watch the runnings away from the beach. There are a bunch of 30 minute up to a couple hour little slices of life all around Negril. Little Bay, Cave Valley over to Moreland Hill, Spring Hill, Jurassic Park.
Have fun, you have opted for a freedom that most do not experience.