found and joined this site initially because of this thread.
i have almost no experience in lawn care. but i have been pulling boats and trailers since before i had my license. one thing i can suggest is a spare trailer hub, greased and ready to go. try changing a hub on the side of the road on a sunday in the sticks. its hot, your boat is swaying from the butthole drivers not moving over enough and that pathetic scissor jack is doing little keep the trailer from crushing your legs.
jack stand, like a floor jack.
hub and spare tire.
4 way tire tool.
and don't buy cheap ass tires.
carry at least a rachet strap big enough to lift the axle for you to limp home.
obviously, i'm scarred. i know guys that pull boat trailers all summer and never grease the hubs, much less repack the bearings. those little bearing buddy's from wal mart only bathe the outer bearing, not the inner bearing. me, i pull my aluminum mud boat for one summer and the hub locks up on the interstate, going 65mph.
more to come as i recall them... take care.