We're constantly traveling 2 or more hours to various lakes, often staying overnight at local campgrounds. Never had a problem with hookups or vandals. That said, I always lock all the compartments, remove all electronics and store them in the truck, and always put the cover on the boat. Most crimes are crimes of opportunity, so making it a PIA to even get inside the boat, let alone fiddle with locked compartments - all while the boat is hooked up to the very camper we're staying in - seems to be enough of a deterrent.
As for traveling long distance - yes, ensure the bearings are in top shape. Stop every 1-2 hrs and feel them to see if they're too warm. It could save you a disaster on the road.
Also - and this is critical - never rely on tread depth to determine whether or not a trailer tire is "good". They can be well past their prime and still have plenty of tread on them. Instead, go by age. Tires need to be replaced every 6-8 years, regardless of tread depth. The rubber gets old, and the sidewalls wear out. I know many guys who've had blowouts that said, "And there was plenty of tread left! I don't get it." And when I ask them how old the tires are, they almost always state longer than 8 years.
I replace my tires every 6 years, and have new brakes installed every 10 (and I mean a complete break overhaul with all new parts, not rebuilt).
I also always trailer with the cover on. I know many guys with cigarette burns in their seats from OTHER motorists tossing their lit cigarettes into their boats while going down the road. Plus traveling with the cover keeps the boat clean.
