The biggest thing you need to keep in mind is that if someone really wants to steal it- they're going to. All you can do is make it as difficult as possible and reduce the chance that you'll become a victim. Ultimate these thieves are gonna steal a boat when they want to. Will it be yours, or the easier-target down the street? It's 100 times more likely that the trailer will go missing rather than just the boats. Stealing a 16' boat will require that they have their own means of transportation and lifting a boat and then securing it to their own vehicle is MUCH HARDER than hooking up the trailer and driving away.
I specialize in crime-reduction so I've got a lot of tips for you- some of them are over-the-top but ultimately you gotta do what you can to protect your investment.
1- Keep your trailer/boat in a well lit area. Is it parked next to your house? Near a shop? In a back-alley? Put a high-powered motion sensor light covering it and the area. And while you're at it, a clearly visible dummy-camera (or 2) will do just fine too. Installing these will be cheaper than you think, and you can always get battery-operated lights too. And put the $200 cover over it, so they're not 100% sure what they're stealing! Thieves will go "window shopping" before they steal a boat of this size. It's rarely going to be a "crime of opportunity".
2- Put things in front of your trailer & boat! Thieves will "scope out" potential things to steal. Can they back right up, snip your chain/lock, hook it up, and drive away? Then it'll be an easy steal and you're a big target. But if they have to move a bunch of crap first- pallets, storage totes, turn the trailer around, etc, then they will consider committing the theft from a different victim. And who wants to walk away with a boat when they have to portage it over a collection of junk and debris? I personally have my trailer turned around (it's easy to move by yourself when not hooked to the vehicle) and then a small utility trailer in front of it, blocking direct access to the driveway. Takes no time at all to move things out of the way by hand when I want to hook up.
3- Put noise-makers everywhere. Literally everywhere. Bells are fantastic. Hook them onto ever rope, line, and attachment point. Go down the the dollar store and pickup a 20 pack! Who wants to steal an item that goes jingle-jingle-jingle from 20 different places as soon as they bump it? You'll know where they all are- you can remove them in 30 seconds! They can't.
4- Take the wheels off of the trailer! Leave it on blocks! Even with a hand-held, cordless drill, removing/installing trailer tires is SUPER EASY. And then you can put the tires wherever. They're small enough. In the back of your vehicle, in the front-entry closet, in your shed... This is the biggest and easiest way to prevent boat/trailer theft.
5- Talk to your neighbors. Let them know you've got a nice boat there and you don't want it stolen. Ask them to keep an eye out when you're not home. Tell them specifically that if they see a suspicious person or vehicle, go stand in their driveway and be visible, and start taking pictures! (Extra points for a photo of the license plate, or their face). Nothing will get a thief to high-tail it out of there quicker. And "Theft" is a lot different than "Assault". So people/neighbors should never worry that an altercation is going to occur, unless they're the ones that run in swinging. That's peoples' biggest fear and it's ridiculous. A thief is there to steal and item that they think isn't being guarded. A thief is not there to cause altercations with strangers, and will leave the area every time unless physically provoked.
6- Record your serial numbers! And add things that'll identity it as "yours" if someone removes the serial numbers. Stickers in weird places? Check. Sign your name in marker on the inside of the cargo compartments? Check. If it gets stolen, call the police and they'll add it to their database. Have a picture of the boat, and have a picture of how it looked when it got stolen from your driveway. Being able to hand the local police department a photo of your boat, on your trailer, with the boat cover attached, will help TREMENDOUSLY as they can distribute this photo to all sorts of different agencies.
And I realize you said you are going to be leaving them in motel/hotel/camping parking lots. Again, consider adding bells and whistles as "noise makers". Add 20 extra, unnecessary straps. Use a boat cover! Consider removing the wheels. Consider turning the trailer around if it's unhooked. Park in well lit areas. Ask other campers/hotel-guests&staff to keep their eye out. Don't leave it in an unknown location for more than a day or two. It almost certainly won't get stolen the first night. But it'll be scoped the second night. And stolen the third.
Best of luck, and enjoy the ride.
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