Great advice in this thread.
After getting a boat/trailer a few years ago my very meticulous/mechanical-genius and father in law asked. "How'd the bearings and races look when you serviced the hubs?" "Serviced the hubs?" I could hear his palm slapping on his forehead. Heard enough trailer tales of terror from him and some rafting buddies that I started to take hub/bearing maintenance very seriously.
The only thing I have to ad to the conversation is that after servicing my hubs I've started carrying a fully assembled and lubricated hub, a small grease gun loaded with compatible grease, spare grease caps, and a small toolkit whenever I'm towing. Would much rather just slide a new hub on the spindle and secure it in place than try to repack/replace bearings on the side of the road or a parking lot.
Even if you think the spare-hub thing is overkill (which I'd happily concede), writing down the part number for your bearings, races, etc and stashing the list in your glovebox isn't a bad idea.