Boat/trailer winch

My tiedowns are just welded on 1/4" flats with holes.

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Maybe extend your rails out with some flat?
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That's a good idea Dave, I may look at doing that. The reason I asked is I bought retractable straps to replace my buckle straps but they need to be mounted/bolted on and would be mounted "under" the boat if that makes sense.

I can't quite see from the photos, but it looks like the rear of the boat is overhanging the bunk it rests on. That's not a good idea, as it travels down the road it will eventually dent the hull right in front of the transom. The entire rear of the boat should be on the bunk. Your boat looks almost exactly like mine, and I wouldn't worry about tongue weight increasing. I had to move my boat forward for the same reason and it amounted to nothing for handling or tongue weight.
Thanks Zach, no the boat doesn't overhang the bunks, they are flush with the back of the boat. But like Del said, it may involve moving a bunch of stuff fwd with it too.

To add, i made a transom saver that stays mounted to trailer, mount consisted of something similar to a 1/2” drive universal joint. And a hook/clip to hang it on. The guys kept losing them, once they were permanantly attatched they never lost them and always used them. Typically it was common to haul them on 50 miles of gravel roads.
Frank, I have a transom saver that's mounted to trailer. Works great but gotta climb under everytime unloading and loading boat. Got a pic of yours?
Thanks all