It looks to me as if the orange colored material is a slightly conformable, kind of rubbery, material that is the seal and the two hose clamps are meant to be adjusted to act as a seal. That joint should be above the static waterline so that it only has to deal with a small amunt when the boat is heeled. The delrin, white washer is meant to stop the rudder from falling out of the boat when it is on the hard. It would be really easy to replace it as it is well above the waterline. When in the water the rudder should be wanting to float up into the boat and there should be a small gap between the delrin and the SS plate held onto the rudder shaft by the cotter pin.
If the rudder is not floating up it may have become waterlogged. If that is the case, and it is not unusual, it needs to be dried out and sealed.
Bill
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I’m sorry but I don’t know what the rudder shaft on your 1990 350 is made of. On my 1995 42s7 the shaft was a composite.
That tube from the bottom of the boat up to the seal should put the seal above the waterline.