Re: terrifying first experience! first time boat owner!
NJ uses the America's Boating Course, offered by US Power Squadrons and the Coast Guard Auxiliary. The intention of this course is to educate boaters on boat operation, not trailer operation or driving skills. That would fall under basic driving skills and driver training. Trailer towing is covered to some degree in the NJ Driver's Manual. It does not cover boating or boat trailering but will cover the rules of the road and the use of safety equipment and required trailer equipment.
I think it may be hard for some of us here to imagine not knowing how to properly trailer a boat, but for those that just simply never have, its about the same as putting a bus driver in a plane cockpit and expecting him to fly a plane. Most of the regulars here also seem pretty well mechanically inclined, for those who are not, the simple things can be trying at best.
I've got a buddy that has a two masters degrees in engineering yet can't remember how to hook up a trailer or even put air in his car tires. He owns a boat which he trailers, and I can't count how many times he's either driven away and dropped the boat off the ball, which wasn't latched properly, or forgot the receiver pin, or connected the 4 pin wire connector wrong and blown the turn signal fuse. Backing up and launching is another story, he's jack knifed it a half dozen times, once so bad he did $1800 worth of damage to his truck, he twice backed in so far the truck stalled, and 7 times that I know of, backed in so far that the trailer went off the end of the ramp. He's left the plug out nearly every time. But ask him what 44,889 x 33 is and he'll rattle off the answer in seconds.
I'm not saying the OP is in this category, but there are those that just don't see how things work. Just the same, don't ask me what a scrub nurse does, I wouldn't do the job, I wouldn't want to work anywhere near a hospital or around sick people. It's just not my thing.
The best way to figure out what works is to do it, often the best way to learn is by repetition and experience, not being shown or told. After about 25 years of dealing with boats and trailers, and many people who are doing it for their first time, is to let them figure it out on their own.
I had a guy that bought a boat from me, he showed up here with a Suzuki Samurai thinking he was going to tow home a 21' boat. He even went out and bought a hitch for it. When I asked him if that was the only tow vehicle he had, he told me he had just gone out and bought it so he had something heavy duty to tow the boat he bought. In his mind, that tiny truck was heavier than the full size Ford van he drove before. The salesman told him so.
I pulled the boat and trailer out on the road, I let him hook it up. After about 20 minutes, he came back in asking what he was doing wrong, "The boat won't fit the truck". I walked out and he was trying to hammer the coupler down over the ball without opening the latch. I checked the ball size, luckily, and it was wrong, I gave him the right 2" ball, and loaned him a wrench to install it. About 15 minutes or more later, he was back, not being able to get the old ball off. I swapped the ball, I torqued and installed the cotter pin and let him hook up the trailer. After I saw he had the ball attached, and wiring in place, and had hooked the chains up, I walked away, only to watch him put the tongue jack back down, (after I had flipped it up). I told him that it had to be up to tow but there was no explaining why. He drove away with it down. He was back the next day to have me install a new jack. He wouldn't listen to me, but figured it out for himself that it had to be up on the road. He read that part on the box from the new jack.
The same guy has now bought 4 boats from me, he's gotten better at hooking up the trailer, but still can't drive or backup. He's crushed two boats, ripped off two wheels, bent 4 axles, and backed into his house and other car 7 times. The worst incident he had was backing down a boat ramp, and having one wheel of the trailer on the boat dock ramp, and subsequently backing down the ramp with half the trailer on the floating dock, thus dumping the boat and trailer on it's side. The boat, which didn't have it's plug, sank at the dock, which he didn't notice until the tried to move the boat over to right the trailer and realized it was sitting on the bottom on the ramp.
I've learned not to answer my cell phone on weekends after that one.
I'm not a dealer, I just buy and sell a few boats every year to pay for my hobby. I don't choose who buys a boat, and really can't consider myself responsible for teaching someone how to launch or trailer a boat. The majority is common sense, the rest is being able to learn and most people learn best on their own. Meaning most people only learn the hard way.
The best advice to the OP is to have someone show you how, the do it over and over again until it's second nature, both hooking it up, and driving with the trailer attached. The same for launching the boat and getting used to how far to back in or not to back into the water. Don't let the truck go swimming, don't trust anyone else to hook up the trailer, don't trust or assume that anyone else has done anything correct, even if they are capable, sooner or later you will regret it.
When you get it all fixed, take an hour or so and practice, till you can do it in without thinking about it. The same for launching the boat, go to the ramp on a slow day and figure it out and get it right, take notice to how far in the trailer is, how far the tires are submerged or where the water is on the fender. Make a note of what works and what don't till your confident that you can get that boat in and out of the water without having to think twice about what you need to do. Get into a routine of when to put the drain plug in as well. For me, it goes in the minute I hook the boat to the truck in the yard. When I get to the ramp all I need to do is unstrap the hull and flip up the seats and back in.