Greg,
 
I don't know anything about the history of your boat or the year, but what  
you have looks nothing like anything I've ever seen on a R22. That being said,  
treat the tiller handle like any other wood project. Sand it smooth. Fill in 
the  gaps with wood filler, sand smooth and apply five or more coats of marine 
grade  varnish. Hanging it will give you the easiest way to apply the 
varnish. Do not  use paint. Paint will chalk and get on your clothes and hands and 
you will not  be a happy sailor. Make sure the tiller handle is extremely dry. 
If it's been  sitting in your garage, take it inside your house and allow to 
dry for a couple  of weeks. It should make it through this season if it's not 
rotten.
You might want to consider contacting General Boats and purchasing a new or  
used rudder and a new tiller handle made for this boat. Yours has had some 
very  bad things done to it. It may work, but it will not work as it was 
originally  intended.
 
Rummy
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