Pulling the 225 is one subject, STOPPING it is another. The boat and trailer outweigh your Toyota by a good bit so trailer brakes on both axles is a MUST. I think you will be working that V6 pretty hard towing. Depending on how your trailer is set up you may have some pretty heavy tongue weight that could be an issue too. I like to see about 10% of the trailer weight on the tongue. Highway trailing will be pushing it due to the wind drag from the large frontal area of that boat. The ramp question depends on the ramp you will use. Factors such as the angle, surface type etc come into play. I assume your truck is not 4wd since you didn't mention it. If it is 4wd than 4 low would help a bunch to pull it up the ramp.
Pulling the 225 is one subject, STOPPING it is another. The boat and trailer outweigh your Toyota by a good bit so trailer brakes on both axles is a MUST. I think you will be working that V6 pretty hard towing.
Nice! Did you get the livewell drained?