Trailering gets easy with practice, I have years of experience with race cars, and even more in the military towing, so backing a boat down the ramp was easy. Size makes no difference really. I hate crowds though so when launching I do it during off peak times, or rig the boat nowhere near the ramp, and just launch like a power boater. With the new boat I did it in really crappy weather because I was worried about the much deeper draft, and my home modified trailer
But it turned out to be just as easy to launch as my last boat, just had to get a little deeper in the water.