How about sharing some incidents of boat & trailer maitenance for new owners out there.  

For instance shortly after purchasing my first bassboat (used) I noticed dark water spots on the console.  Was water in the lower unit of the trolling Motor.  Or Grease thrown on the rim of the trailer wheel. My bearing bra was leaking grease, but I didn't make the connection that the bearing might now be partially filled with water.  Duh!

Feel the trialer wheel for heat.  They should be just a little warmer than the air.  If they are hot to the touch, you're in need of new bearings.

Let a pro maintain your bearings unless you are pretty good mechanically speaking.  It's not worth the hassle of doing a poor job or seating a bearing incorrectly.

Lug nuts can loosen.  Check them every trip.  Also check the nuts and bolts on your outboard. I nearly lost a motor last month on the interstate last month, and had I not checked them at a service station, I could have been involved in a fatal accident.

I watched a guy lose his outboard on the highway, luckly it was his secondary trolling motor, but it had to be at least a 15hp motor. The motor looked trashed.

I imagine that the road vibration losen the clamps.