All of my trailers, my boat trailer included do NOT get bearing buddies. They have caused me way more problems than they have solved. I now use a greasable spindle. The dustcap has a rubber plug that once removed, allows greasing of a zerk inside the cup on the stub end. The spindle relief hole is inboard of the greas seal, directing the grease through the bearings back to the dust cap.
I service this every time I dunk my trailer (at least 4 times per week) and have only had condensation inside. The grease forced out is wiped up and the cap replaced. Fast, easy, effecient.
I do repack my bearing twice a year for peace of mind, and replace every two years. I put about 30K a year on my trailer.
The proble I had with bearing buddies was that by putting grease under pressure and holding that pressure, was next to impossible. You go down the road, heat the hub, and the grease/ air trys to expand. It pushes out a very small amount of grease. This allows the diaphram to rest against the outer edge of the BB. Dunk the trailer, cool hub, suck water. I was repacking bearings once a month, trying to get the milky mess out. This is all freshwater mind you.
And my brakes are always clean. Except for a little sand or the occasional gravel, they are never fouled.
Dave