I have an F206LS with the stock ski tow ring on top of the transom that seems to leak a small amount of water when it rains. My canvas has a cut out for it so the water can migrate down and thru this into the bilge. My question is should I try to seal this or is it best to leave it the way it is and drain when I take the boat out of the water? It looks like the water drips onto the outdrive shield and than works its way to the bottom of the bilge. Is this normal? The boat has spent most of its life in a dry climate and now it is moored on a lake in front of my home. Any advice would be appreciated!

If it leaks fix it. If the water is moving through the transom then the coring might be getting wet.

My 206 is exactly the same way.
The tow ring is not tight against the transom, but is held out by one or two braces and then the top stainless plate. The hole that it passes through is not sealed and will allow a small amount of rain water through. Nothing to worry about.
My cockpit cover fits (or used to fit) the same as yours. I know have a full length cover.