Structural damage to hull during winter lay-up

Once your boat gets back into it's natural element (water) the hull will relax and any indentation should correct itself.

If there is any repair work to be done I would do it once the boat is back in the water and had a chance to resume it's normal shape.

After over 10 years of owning a sailboat I have had this happen several times over the winter with our cradle. It has only been a minor annoyance, at best.

Next winter haul out be sure to remove both sails from the boat and try to be there when they do.

Your hull will regain it's normal shape and probably has with the addition of those 2 jack stands. By the way, those jack stands are improperly deployed: they are supposed to be chained together at ground level and used on opposite sides of the boat.

Your leaky rudder is a different story and not likely not caused by your boat yard. It was a farging cold winter here reaching down to 0F a few times so you likely have some ice damage inside your rudder. How bad is it? Hard to tell.

At a minimum you might consider barrier coating your rudder with epoxy and filling & fairing any obvious entry for water into the rudder.
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