I went through the same experience with bearings on boat trailer. First left side, next year right side. The hub/drum had 6 bolts. These hubs/drums are available with smaller or larger outer bearing. The original had smaller bearing, replaced with hub/drum with larger bearings. Took me several years to finally solve the problem:
-converted to disk brakes. Disk brake hubs come with large bearings. With disk brakes you can observe hub seals without removing drums.
-better braking
-you can service brakes without removing drums&bearings
-install bearing Buddies. Fill properly with synthetic grease and you don't have to worry about repacking bearings annually
-use SKF or Timken bearings. The Chinese bearing were falling apart after as little as 500km even with synthetic grease.
-installed spindle sleeves(not cheap). Only with magnifying glass I was able to see corrosion damage on spindles in an area where hub seal contacts spindle.
Good quality stainless steel bearing buddies have a blue plastic ring indicator which starts moving when hub is full of grease. If it moves back in, add grease. Keep adding until all air in hub is replaced with grease and plastic indicator stick out about 1/8". When hub heats up after long drive, blue ring will stick out more and will move back in after cooling.
Adjust bearings properly:
-tighten adjusting nut to 50ftlb while rotating wheel by hand
-loosen adjusting nut
-hand tighten the nut
-insert cotter pin or loosen the nut to line up with nearest cotter pin hole
There is no justifiable reason for repacking trailer bearings every season. You don't do it on a car or truck. If done properly as described, there should be no reason to do it every year.
There was a good article in recent issue of Trailer Life magazine about disc brake conversion. I am elated that these kits are finally available and I think everybody who has any trailer with brakes should consider it.