Re: How a boat is suppose to fit on trailer
From your photos, I think that trailer is too small for that boat. What size tires are on it?
It looks to me like the winch tower is right up next to the hitch. It also looks like the stern of the boat extends past the rear crossmember of the trailer.
That's what I'd be concerned about with that rig. With a tongue that short, backing is going to be difficult, and if those wheels and tires are as small as I think they are, they're way overloaded with that boat.
Bottom line is that I'd look very closely at the weight limit marked on the tires and have a look at that boat on NADA to see what it weighs. Then add in the weight of engine and gear. I suspect you'll find that it's not a good match.