Good call! You were about 1 trip short of a call to BoatUS Trailer assist! You do have BoatUS Trailer assist, don't you? Costs $14 per year. My last assist would have cost $600.
BTW - I do my bearings every year - do minor inspections - examine grease/oil, check for wheel wobble or thrown grease inside the tire every 4 or 5 trips. Even then, "chit" still happens.
I do those checks on a regular basis along with checking the hub temps after every trip. Wierd they never got warm. I do have trailer assist but not really wanting to need them.
The South End provides useful resources and discussion forums for those that fish The South End of Lake Michigan for Salmon, Steelhead, Perch, and Bass as well as elsewhere in the Region and Chicago area.