Sounds Like You are Committed
So lets focus on making this work
Here are some tips, by no means inclusive and some of the less obvious tidbits I have learned, some the hard way.
Bumper protection, cut a piece of plywood to place in front of the rear bumper resting on the draw bar, mine even is notched so it stays put. this will serve to protect the bumper from the trailer coupler. Use it not only for hooking up to the trailer but when uncoupling. The trailer may roll forward a bit biting a chunk out of the bumper. Start looking for a bumper sticker to place over the calamity just in case.
Put the largest wheeled tounge jack you can find on the trailer. This will make it easier to move the tounge to drop it on the ball instead of trying to move the car an inch and a half forward and three quarters of an inch to the left.
Tounge weight, first move stuff in the boat forward. Moving 10# from the stern to the bow is the same as as adding 20# to the bow better because you added no weight to the boat. The motor can hang on the ladder at the front of the trailer rather than in the car.
Make sure you have a spare tire a lug wrench that fits the trailers lugs and a jack that will fit under the axle when the tire is flat. Do not jack up the trailer from the frame. the frame is not built for the stress point the jack puts on it.
Pull the boat ALL the way up the winch post and secure the boat to the trailer at the stern and the bow. The winch strap is not a secure enough tie down for the bow throw a piece of chain with an S hook around the post and to the bow eye.
Pin the coupler locked, it really sucks when they bounce off.
Your surge brake coupler should be pulled back out when ever you leave the trailer if left pushed in the exposed portion of your wheel cylinders and master cylinder will rust and lock up your brakes.
Perhaps most important grease often, check the tire pressure religiously and stop frequently to make sure everything is secure and the hubs are not getting hot.