Which is easier to maneuver, 25ft+20ft, or pickup+30ft FW?

With practice any setup in comparable length will get easy to maneuver.

The problem will be if the roads are too narrow or turns too tight. There is a point with any setup where it is impossible to get where you need to be no matter how practiced you are. When you run into something like this then you either find someplace else to park or use some other means to get everything parked...like take the trailer in to the spot using a forklift or powered trailer mover and then park the truck or B+