Yes, the thread slowly evolved because one comment lead to another and we got sidetracked by safety issues. Apologies for that.
So, I reviewed the pictures a little closer. To answer your question, the boat should not stick out beyond the back of the trailer. Your trailer is too short. However, due to the boat'slight weight, you probably can move the winch post a couple feet forward to put the transom right at the end of the bunks. That will give you a little more tongue weight, which can only be a good thing.
Also, by the looks of the bunks, your carpeting is shot. That certainly adds to your launching problems. Replace it with ezslides and the boat will launch like a breeze and you will only need to back in far enough to get the trailer tires wet.
If my assessment is wrong because I misinterpreted the photos, provide a better view underneath the boat.