Re: Trailer bearings
angler, go ahead and get into your hubs. It's not that difficult and you'll benefit in all sorts of ways. First, you'll learn exactly what size bearings you have. Second, you'll see for sure with your own peepers what condition everything is in. Third, if you ever have to perform emergency surgery on the road it will be much easier if you're familiar with your setup. Here's my SOP. Feel free to modify or ignore as you see fit.
Hook the rig up to your TV. Jack up one side of the trailer just high enough that the wheel will spin freely. Crack open a cold one. Spin the wheel with your ear close to the hub just to get an idea of what it sounds like, then remove the dust cap, pull the cotter pin, remove the castle nut, washer, and outer bearings and place them all on a clean shop towel. Wiggle/pull the wheel until it comes off the spindle. At this point I like to lay down another clean shop towel and sort of bounce the tire/wheel over it until the inner bearing falls out onto it. Once you've done that inspect the inner seal for any leaks and replace if necessary.
Next, remove as much of the old grease as possible, then repack the bearings. There are tools for this, but I just put a glob of grease in my palm and slap the bearing into it while slowly rotating it (bearing) to insure even grease intrusion. Drop the inner bearing back into the race (which will still be inside the hub) and slide the wheel back onto the spindle. Repeat the packing procedure for the outer bearing, then put everything back into place. When tightening the castle nut I like to hand tighten it then snug it down a little more with a wrench or channellocks just to be sure everything is seated properly, then I back it off until there's a tiny bit of play in the wheel. Put the cotter pin back, give the wheel a spin to be sure everything's free and easy, then replace the dust cap, apply the grease gun to the zerk, and fill 'er up.
If you have bearing buddies stop pumping when the spring loaded plate (you'll recognize it if you don't already know what I'm referring to) almost reaches the outside of the cavity, otherwise you'll blow the inner seal and lose grease as you travel. You know what that means.

:facepalm:

If you have the sure lube type configuration (zerk on the end of the spindle) pump away until grease oozes out the front of the cavity. That's pretty much it. Sorry for the info overload, but I'd rather overload than underload you.

Good luck and welcome to iboats.
