Trailer into water more
I have a 170. But, like the 140 it's trailered, at least twice a year. The solution to the winching problem is simple. Put the trailer deeper into the water so that the boat is just barely not floating when winched completely in. That way, the winch does not have to pull up as much weight, the eye on the front of the boat does not have to take as much stress, and everything is less likely to bend or break. Same in reverse when launching the boat. The boat should be practically floating when unwinding the winch for launching. If the trailer gets wet, it will still work fine afterwards. The boat also slides better when it and the trailer are wet.