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I recently inherited a 1964 (maybe 1965) wooden kit sunfish and I have a couple of questions. First I will tell you that the boat has not touched the water in 35 years, I have the original sail, daggerboard, rudder and all other hardware. The boat has been stored in a tarp under a poarch in my grandfather's house in Deleware, somehow this has prevented rot from what i can tell. The hull feels solid but all the paint is cracked and chipped. I have spent the past week sanding and putting wood filler in all the nail and screw holes (I have drilled out all of the old filler in order to replace it).

1) Can you race a wooden boat that was made at home?

2) If you can't race the boat then I want to make it a bit faster (I'm 17, speed is key), What is the best way to do this. ex. More sail?

3) Will a longer, narrower daggerboard allow the boat to power up more.

4) The transom of the boat is very nice, so i wanted to remove the old rudder and set up a thru the hull rudder, will this allow the boat to go faster?

5) what is the best finish for a wooden sailboat? Should i use special marine paint?

Any help or advice is greatly appreciated

Sounds like you want to make a Formula Ford from a Pinto. In the process you will most likely end up with nada.

Go here and look at the ISCA Rules http://www.sunfishclass.org

You can race but the Sunfish is a One Design Class. That's means stock.
It will be like bringing a 1964 Chevy to a 2006 NASCAR event. Even if you put on modern tires you will be at somewhat of a disadvantage.

Don't get me wrong, you can race at open sailing events and have fun and gain knowledge doing it.

The fastest thing you can do for your boat is add a can of practice and a box of skill mixed thoroughly with two gallons of knowledge. Apply this liberally to the deck, tiller and sail.

You can find the recipe in a book called The Sunfish Bible. This group can provide lots of cooking tips.

I'm afraid when you start to put hot sauce and anchovies on your cheese cake like you have proposed to do you'll chase some of the chefs out of the kitchen.

Google Jamestown Distributors and check out the paint section. They have lots of options for good finishes to put on your boat.
Your boat would be completely legal to race so long as all the parts used are provided by a Sunfish distributor at one point or another, aside from those specified in the rules that are open. Welcome!

Most people with boats such as yours are working to preserve them, and your sounds like it might be museum grade! Sure you can sail it, but I would consider recreational sailing rather than racing, as if someone misjudged and you had a collision, I'd hate to see splinters from an aluminum rub rail on the wood.

If you want to race, mow a few lawns, save up $1000 and buy a fiberglass Sunfish. You'll find years and years of enjoyment, your appreciation of your ancient woodie will grow over time, and your lifetime enjoyment of both will surprise you. Check with your Regional Representative to learn more about racing in your area. Sometimes someone will loan you a boat to help you get started. Good luck with your project.