Hey there Learnin to Fish - You have a very common issue at hand, you are backing the trailer too deep in the water. Whatever depth that you use to gently float the boat when taking the trailer off, you should be less deep when putting the boat back on. The boat needs to contact the trailer boards and then it will raise the bow of the boat and you won't have to fight it.
Capt. Craig Copeland
Licensed by the US Coast Guard
2013 Nautic Star 2110 Shallow Bay Boat
Humminbird HELIX 12 CHIRP MEGA SI GPS G2N
Nautic Star Boats Pro Staff (nauticstarboats.com)
Redneck Fish'n Jigs Pro Staff (redneckfishn.com)