I have a 19' fiberglass boat that is fairly heavy for its size, and tow it 1500 miles round trip every summer. I don't know the total weight, but the bare boat is 2500 lbs. Throw in motor, batteries, trailer plus stuff and it is pretty heavy. I have a 2wd V8.
I have a dual axle trailer that has surge brakes on one axle. Its not unheard of, but boat trailers that get dunked in the water rarely have electric brakes.
I tow with the trans in 4th.
Tips: Always have a spare tire with you, and a way to jack the trailer. Even better is an entire spare hub/wheel/tire assembly.
Every stop, walk around and touch the hubs and tires. Anything more that a little warmer than air temperature means that something is going south.
I always run with the trailer tires at max pressure. (50psi in my case)
You want the tongue weight to be around 10% of the trailer weight, so having a tongue jack helps a lot. If the tongue weight is too light, the trailer will have a tendency to sway (not good in an emergency maneuver). My dual axle trailer is much more stable than a single axle.
With the tailgate open, I can stretch a little and see the ball of my hitch as I'm backing up. Makes it easy to back right to the trailer without having to get out and look.
I always unplug the trailer lights before I back into the water. The lights will last longer that way.