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I'll try. I have a 14' Skimmar, 1972. It was given to me, hull and mast only, and has a retractable keel. I took measurements and bought a used sail online that is a perfect fit, then picked up a used rudder and an old mainsail from a junkyard that I turned into a working jib. Then the rigging...
For months I despaired, so I asked around. 2 or 3 times I was told to get Royce's Sailing Illustrated, Volume 1 and finally did. The diagrams in there were FANTASTIC! I literally had her rigged the next day, using the illustrations a bit of common sense (in short supply in my family : ) and experimenting in the lightest of winds. YOU CAN DO IT!!! I practiced my rigging in my own yard with the boat tied down and on a trailer. I cannot recommend this book highly enough.
I pretty sure you didn't want a "buy a book" answer, but I've referred back to this little gem innumerable times and it was some of the best money I spent. Tell ya what though: in the spirit of sailing brotherhood if you ping me back I might be able to sketch/copy/scan a helpful page of two, because I know exactly how you feel.
 
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