Jake, here's what I've done for a 14' aluminum with electric motor:
At home, with the boat empty,
1) I pick up the trailer and hook it to the wonder truck. I add the empty cooler between the proper seats.
2) Oars, life vests (make sure you have a WHISTLE, and a spare "safety" paddle/oar, as its required).
3. Add batteries to the back end of boat, w/MOTOR, Some like to take the batteries but no motor, but you don't have to imitate them. Have your Boat REGISTRATION & Fishing licenses.
4. Before leaving home, do 3 things: A: check brake lights
B. Have plug in back of boat, and a spare plug. in the boat. C. Make sure the (gray) Nylon safety strap is holding boat on trailer
5. Load vehicle with ice, food, coffee thermos, bait (if you forget the lunch you can eat some bait), water jugs, all tackle, HAT!!!, coat & rain gear, fanny cushion, flashlight/lantern as necessary w/batteries, pocket knife, needle-nose pliers.
6. At the res, I back down the ramp, tail gate down, to water's edge. With boat unloaded & light, I start to push it mm......18" or so off the back end of the trailer, then I put most of the gear in. With the trailer hook unhooked, I attach the BOW-LINE of the boat to the trailer!!!!!!!!!!!!!!!!!, then give the truck a little gas and slam the brake about the time the trailer lights touch the water or thereabouts. The boat slides off and I can hook it to the dock for more loading etc (I've taken to greasing the rails with clear petroleum jelly to help it all slide)
7. Park truck, hit the restroom, jump in the boat, motor away and hook on bait
RETURN.
A. Tie boat at dock & retrieve truck, putting the brakelights close to , running the hand-winch line with hook a few feet past the end of trailer.
B. Leave all gear in boat, motor it up to the trailer and grab the winch hook & attach it to the boat. I'm agile enough to jump off the bow and walk UP the trailer like an acrobat pulling along with the winch line, then winch the boat up all the way.
C. Put gray nylon safety strap & motor away
[if I forgot something, I'll add it, and others can help you make a good checklist]