Got one trailer when I pull it and put the brakes on, it sounds as if it is squealing as in not being greased, when in fact I do grease them every 2 weeks? Any ideas or suggestions?

Is the air ballanced in both tires on the same axle? If one tire is low and the other tire is proper air pressure it will make that noise.

Brake squeal is usually caused by a friction issue between the brake shoe and the drum; cheap brake shoe lining, glazed lining (from overheating), worn-out brake shoes/drums, polished drum friction surface, etc. Check the obvious things first like brake adjustment, leaking wheel seals, mud/sand/etc behind the dustshields in the drums.