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Once you're out in the current, it affects your whole boat as a single object (equivalently, there is no current and the coastline is moving past you).

Was the tiller much harder to move in one direction than the other? What were the conditions, and how much canvas did you have up? If winds were above 15 knots and you had full sails and were beating upwind, it's likely that it was just weather helm (lots of other threads on this topic). Maybe when you got into Raccoon Strait, you were in the lee of the island and felt less weather helm. Next time, try reefing earlier. If you haven't thought to reef, you can try sheeting out or bearing off, either of which will depower the sails.

Another possibility (something that happens pretty often on my boat due to the cockpit layout) is that some line or other got wedged behind the tiller and is acting sort of like a doorstop. On my boat, it's usually the mainsheet and sometimes the traveler (mounted right behind the tiller).

There might also be something fouling the rudder, like fishing line. Seems unlikely if you had a diver look at it, but he could have missed it.

Also, what is your rudder setup? Is it transom- or skeg-mounted, or is it the spade variety? The latter, in which the rudder pivots around its centerline rather that the forward edge, is supposedly easier to steer.

Beyond that I couldn't help you. Tiller steering is pretty simple. I think if you have ruled out everything else, you'll have to haul the boat and drop the rudder to look at the post and bearings and what not.
 
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