First and foremost, lets look over the always neglected trailer before we make any trips huh.
Saftey chains.
Couplers.
lubed bearings .
lights.
TIRES TIRES TIRES!
Check your fuking broken down ass tires!
feel free to add

-beerjet-
Check your wiring, stuff some petoleum jelly into the connectors, check for hanging wires and piss poor connections (Like the el cheapo quick connectors). Don't forget all tow vehicle inspection points. Check your receiver bolts, ball tightness and hitch pins. Check the hitch and latch itself and oil/grease it up a bit.
Oh and yeah, check your fuking broken down ass tires! AGAIN!
Also check your bunks and fender guards, we don't want any horror stories over something silly like that.
What did I miss Omar?
Ray
Wait, already know what I missed, check for loose axle u-bolts, cracked or missing leaf springs and bad, gone or cracked shackle bushings. Lets face it, most of our boats are old, and so are the trailers.