First off, go for it. An adventure is an adventure even if (especially if) something goes wrong.
All this talk about trailers and no one has mentioned sh#$ brakes and f#$%@& lights...
You'll probably be driving in the dark so make sure your brake lights work with your running lights on. clean & tighten light bolts so they get a good connection. same with the white wire on your truck & trailer. make sure all your little side lights work and your license plate is lit.
I hate trailer lights...
I hate trailer brakes and don't have them but I would if I were driving I95 to Florida with my V20 baby loaded with 2 weeks of crap