Welcome to the Trawler Forum.
If you can put your pontoon boat onto it's trailer in a cross wind, a trawler should be a piece of cake. A friend took me for a ride in his 24 footer and when we got back, jumped off to get the truck and trailer, It took me 3 tries to hit the trailer. They sure do catch the wind!
You never really learn to swear until you become a boat owner!