the trailer itself i'm sure weighs less than 3k... its just a 16ft utility trailer with a wood floor

 

Read this to mean the rating of your trailer, the total amount it is designed to carry. In your case the jeep clearly weighs more than 3000lbs and if you tack on the weight of the trailer you are looking at a hefty fine if something goes wrong. Not to be discouraging, but that is a lot of weight to be stopping with just the trucks brakes. Can it be done yes but your brakes are gonna take a beating.

 

i am almost positive all states, when giving the weight limits for requiring brakes go by gross (fully loaded) weight rating of the trailer

 

what part of ct u live in? i live close to hartford area