Wheel bearing grease and bearing quality

It has been two years now, and two different brands of grease with the same result. It looks like crap in one season and the bearing has either failed or it on the brink of failure. I tried a valvoline synthetic and then lucas sticky red with various brands of bearings. I use a pressure tool to pack and the grease is visibly coming thru. I NEVER dunk the bearings in salt water and rarely in fresh and then only to retrieve. I know how to set the pressure, tighten to seat then back off until there is just enough slack to insert the cotter pin. The inner seal looks pretty good, so I know the grease is not leaking thru there. Finally, I do check the bearing temp after long drives and they are always cool to the touch. Even on a 1000 mile drive to florida.
So what's up? Is there a better brand of grease or specific brand of bearing I should get? Should I get the bearing buddy caps? It makes no sense that a trailer this light is doing this, never happened with my old hobie 16 trailer.

Always use Bearing Buddies on boat trailers. I have for 34 years and have not had a single wheel bearing failure. Due to the boat ramps I use, my wheels always get dunked.

Bearing Buddies work by pressurizing the grease into the bearings, keeping all moisture out.

+1 on the bearing buddies but red grease won't work for boat trailers IMO. I use Lucas Marine grease. Marine is the key but Lucas has added detergents that help fight corrosion. Also don't buy cheap seals. Cheaper ones will almost certainly fail in fairly short time.

Bearing buddies are great, but your failure rate is too high. Something else is afoul.

Things that make bearings sad:
Contamination
Bad seals
Bad races (if you don't replace the inner race with the rest of the bearing, bad things happen)
Incorrect compression

Either that, or your maintenance standards are super high, and what you consider to be a failed bearing is not what I would consider a failed bearing.

Failed bearings have 1 or more issues:
Have play and/or get hot (+40F over ambient).
Don't turn easily, and/or smoothly

Nearly failed bearings:
warm, some play
Turn easily, but have some rough spots
have shiny flakes in the grease

It is not unusual for your grease to be dark/dirty looking. However it should always be free of discrete debris, like sand grains, metal fragments, water drops.

These bearings are way too big for the load of a little kayak and aluminum trailer .. So you have to tighten them up a whole lot more than you would for your dirt trailer. This gives the load they need to work ...and then tighten them again every couple hundred miles. tight to where the wheel won't turn and then back off to the nearest cotter pin slot. They will run a bit hot for the first 20 miles or so.

The bearings were one timken and one no name chinese. Both are locked up, after spraying a ton of brake cleaner in them they do not spin or even rotate. The bearings never even got warm to the touch, and this includes a thousand mile trip to florida pulling at 65-70. I have 12" wheels, to lower the RPM compared to the stock wheels.
Right now I am thinking hubs might not be good. I put new races in every time I changed bearings but if the hub ID is not round it could be the cause. Substituted one hub with a new spare, and will see what happens. I am not sure if my bore gages are small enough to check the race ID but will try that too.
Regardless this trailer is one more cooked bearing away from getting a new axle. I have another trailer used just as a kayak rack with an almost new axle.