IMHO, the winch is not NOT for forcibly dragging the boat onto the trailer.
If the trailer is in deep enough, float the boat all the way onto it, pulling it into the V with the winch strap, and then back off the strap a little ..... or engine drive it onto the trailer until it noses into the V-notch, then take up MOST of the slack, but leave a little. When the trailer is pulled out, and the boat settles onto the bunks fully, there will usually be a bit of space created between the boat nose and the V-notch. That is the time for the "bump" , to seat the boat again into the V ..... ONLY THEN take up all the slack with the winch.
Yup, it's a counter-intuitive thing, but you just cannot expect the boat to settle fully and correctly on the trailer until after it is pulled out. The boat floats on water, level, and the trailer sits on a sloped ramp.
You can't reasonably expect to drag the boat onto the trailer bunks with the winch alone. And you can't expect to have the boat set properly on the trailer when it settles, without breaking the winch, if the winch strap is tight before it settles.
If you just take up the slack lightly with the winch, there will be enough slack in the strap or rope winding on the drum to pull out, but if it's really tight, as after dragging the boat onto the bunks of the trailer, ... well,
The strap can't stretch that much, and neither the strap nor the hull can be expected to defeat the basic geometry of the situation. With the huge pivoting leverage of 28 feet and 3000+ lbs. the winch is almost sure to fail at some point. If the winch strap is snugged really tightly on the drum, it's only over a short distance of a few inches, but that's an averaged torque of about 42,000 lbs. on the winch, strap, hook, eye, and boat-nose , whichever is the first to go. ( It's abuse, so be thankful it is the " sacrificial" winch that fails first in this case. )
Keep in mind that abusing the winch is not the only mistake that is easy to make on the Mac ... you can get the boat stuck on the trailer with the centerboard down a bit in front of the crossmember, swamp the boat with partial ballast, break the steering gear with half-deployed rudders, or chew them up with the prop, break the gooseneck with accidental jibes, ( no joke

) and blow yourself up in smoke while grilling out in the cockpit with the gas cans under your butt.
It's a tricky boat, for sure.