When I lived out west I used to trailer around 10,000 miles per year. Over a 10+ year period, I experienced just about every kind of wheel bearing failure, so I ended up learning a lot.
1. Many of my failures came after having the bearing or hubs replaced by professionals. Several times after a repair the replacement bearings would fail within a 100 miles. The problem is that many shops over tighten them. Boat trailers with disc brakes and surge actuators are not the same as travel trailers with electric actuators (see below). The proper way to adjust the bearings is to use a wrench to snug them up and make sure they are correctly seated. Then loosen the castle nut and turn it clockwise until finger tight. Then back it off to line up the cotter pin hole.
2. If you trailer in mountainous territory and have disc brakes on your trailer, you need to lose the surge controller and replace it with either an electrical actuator or electric over hydraulic. In either case you have the ability to control the amount of braking from inside of the tow vehicle. Surge brakes activate when you are towing down a steep grade every time you touch the vehicle brake or use your exhaust brake to slow down. This overheats the hubs and causes the bearing to fail. I one had to replace hubs twice in order to make it down a long 8% grade.
http://www.boatus.com/magazine/trailering/2013/february/electric-over-hydraulic-brakes.asp
3. Upgrading the axle load capacity to well over your actual boat and trailer weight is a really good idea. I eventually went this route. Heavier axles us larger bearings, which distribute the weight over a larger surface area.
4. I used all 3 types of bearing lubrication systems over the years. Bearing buddies work, but you need to be careful to use double cupped grease seals (the ones with the springs) and to never over pack the bearings. If you keep shooting grease into a bearing buddy hub, it has no where else to go except to blow past the inner seal. The right way to do it is to just add enough grease so that you can rock the metal spring plate with your thumbs. If you pump grease in there after every trip you will eventually have a problem. You should clean and inspect/replace bearings with bearing buddy protectors once a season to get the old grease out.
Spindle lube hubs like EZ Lube or Super Lube are the ones that you should grease after each trip. These do not pressurize the grease and adding a little fresh grease after dunking the trailer will blow out any water that may have seeped into the bearings. I've have these type of hubs now and they are working very well. I don't trailer much anymore, but I pulled the hubs and cleaned the bearings after 4 seasons and they were fine.
Oil lubed trailer hubs are the latest technology, but they have had a shady history. The problem was when people tried to mount oil lubed hubs on used spindles. I tried this using the Kodiak kit and it leaked right away. However, I know plenty of people who have had great luck with this system when it came fitted on new axles. Oil lubed hubs run cooler than greased hubs and the lube lasts much longer between services. The technology is well established on OTR trailers.
Bob, I'd bet that your issues are caused by overheating you hubs coming down the mountains where you live. Once the rollers, races, and grease gets overheated, it's just a matter of time before you have a failure. Heavier axles and an electric over hydraulic actuator should solve your problem.