Yeah, that 1756 is a pretty heavy boat. My 1652 is quite a bit lighter. Like you said, a Carolina skiff 14' or a G3 1448 WOF would be half the weight or even less. You may want to look into keeping your motor since you know it's history and I think most people looking at a 1756 would be looking for 40-60 hp or a jet setup. You could probably even remove the side console (if it's not welded to the hull) and transfer it to a 1448 boat. Regardless of what boat you end up with, you'll want to put side guides on the trailer to help with loading it straight. I had my boat out on Friday and I was able to load it and pull out in under a minute. I have the bunks lined up right along the strakes so it's almost self centering. And I would start with Craigslist or Facebook Marketplace to list the boat at no cost. I've sold several boats through craigslist, just put good pictures up and give good details to minimize the stupid questions you'll get.
Here's a picture of the trailer and one showing our ramp which comes down at an angle and then drops off.
Here's a picture of the trailer and one showing our ramp which comes down at an angle and then drops off.