I had to retrieve a boat one time for a guy who did it like that and the rope snapped. I just happened to be pulling up to the ramp in my boat while he was launching.
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I had a 2 man boat with a trailer with rollers instead of bunks. If I had ever unhooked the winch strap before getting the boat backed into the water the boat woulda rolled off the rollers and hit the dry ramp. My boat would roll back down the trailer before I could get up front (when loading) to hook up the winch strap unless I left it in gear and running (which is something I really didnt like doing with a tiller controlled motor). I dont know if it would work with your boat, but I'd suggest changing those rollers out for bunks. I did and that fixed all my problems.;)
I fish most of the time by myself and also use the rope method to launch. Here are two things to consider before launching, How steep is the ramp and the weather conditions. Last year after fishing on a local lake in the PM I decided to trailer 45 miles to another lake the next AM, the weather temperature was in the mid twentys. When I arrived at the launch some were launching and others were getting ready to launch so I did like wise, undone the transom and wench straps, hooked up my launch rope now I am ready to launch. I began to back up to the launch and just as the trailer tires broke over the incline the boat began to slide and slid almost off the trailer and was still about 10 ft. from the water. With the help from other fishermen we were able to get the boat back on the trailer and I was able to complete the launch. The bunks had a thin coat of ice on them causing the problem. I now make sure the trailer wheels are in the water before undoing the wench strap. Embarrassing, you bet, expensive, could have been, nothing torn up just pride. Good luck and good crappie fishing and you can do it.
I occasionally fish bass tourneys with my uncle. I have seen solo guys stick them 20ft glass boats n the water fast enough to slide off the trailer and ease the boat clear for other boats to launch and then they park their truck and bum a ride out to their boat that is out there floating by itself, pretty cool stuff. I launch a lot by myself. I dont get n no hurry and if I see anybody launching solo I offer to help. The way I launch my 15 42 is back the trailer far enough n that the back is floating and my front winch strap is still attached. I get out un strap get n the boat and motor away from the ramp. When I load I do the same thing, run the boat up on the trailer, hook my strap and pull out.
I have a small fiberglass boat that is just under 14'. I also have keel rollers on my trailer, as well as bunks. The keel rollers will allow the boat to roll right off the trailer quite easily even on level ground. This means my launch/load procedure go something like this;
Prep the boat and back the trailer down into the water with winch strap still attached. I hook a long 30' line to the bow eye and unhook the winch and shove her off. She floats clear of the trailer and I pull her over to an out of the way spot and tie her off. Park and go fishing.
Loading is about the opposite, I shove the boat off the shore and towards the back of the submerged trailer. I use the line to pull her up on the rollers and up to the bow eye and hook the winch on.
Now, on steep ramps, this is a breeze. On shallow ramps, I have to drive her up. Once up I leave the motor in gear (a tiller steer) and set the steering drag level (Nissan motor, has a lever that allows me to control the steering friction, sorta like drag on a reel) to max and with it in gear, walk up and hook the winch up. I kill the motor and climb out, looking something like a beached walrus doing so.