Keep in mind that the same style of bearing setup was used for decades in trailers and the front of every rear drive car/truck with thousands of miles service life. The only difference with a boat trailer is getting submerged.
The reason bearing buddies work so well is the spring and diaphragm keep the grease at a pressure slightly above ambient while not over pressurizing and blowing a seal (as well as not leaving any void between the bearing and cap), this is what keeps water out. They aren't just lubricating.
I also carry a spare bearing and a CAA card.