Donovan;
Benny gave you some good advice. For those, I recognize the winch stand as the trailer was manufactured by KWS or Ken's Welding long gone many years ago. Generally, everything was welded in place, therefore, it would be difficult to raise the bow guides but from the picture if I am see correctly, everything is in proper alignment.
Remember when the boat is floating, it is horizontal and the trailer is at an angle. You will get it up most of the way but as you pull the boat out, it becomes horizontal with the horizontal position of the trailer and the bow will be close but not all the way. You can add items on the bunk boards to make the boat move forward easier but the best way is to winch and then brake, winch again and brake again until the bow rests in the proper position with the winch stand. Make sure of no overhead obstruction to include wires. Do the braking on flat or downhill surfaces.
Also make sure if you have brakes that they work. With the center of gravity high on the trailer the boat will have a tendancy to sway the trailer more which is why the brakes is an important item always to be servacable. I hope this helps you. Also, place as much gear in the V berth vs. the rear.
If you do not have brakes on the trailer as that was optional, should the trailer begin to sway, accelerate a little to stop the swaying and then brake. Never go over 55 mph.
crazy dave condon