BradO wrote: 1) I have a loose cleat on my mast. What is the best way to deal with this. I believe that it is the jib cleat.
You'll need to re-rivet it. If it's loose enough to get a hacksaw blade underneath it, carefully saw off the rivets (don't want to scratch the mast!) and drive the tails into the mast with a punch. This is preferable than drilling off the heads, since the heat generated can melt the plastic cleat. Re-install the cleat (you'll want to get a heavy-duty rivet gun - not from Home D or Lowes)
BradO wrote: 2) If you get water in your mast, how do you get it out? Same hole? What if you capsize and the leak is at the tip. After righting you determine that you have water in the mast, how would you know how to get it out? This is hypothetical, I have not tested my mast for leaks and everything looks good so far, except that one loose cleat.
A small hole drilled in the mast works well. You can seal it up with silicone or a rivet/casing when you're done. Note that there are foam plugs in the mast at the ends, so the hole should be at least 1' from the end. Bottom of the mast is better - it doesn't see the pressure that the top does when the boat is turtled and is less likely to leak.
BradO wrote: 3) There is a 1" gouge up high in one hull. It might lead to a small leak, what is the best epoxy/bondo to use to repair this. It will not take much more than a tablespoon to fill. How do you finish the repair after sanding, is painting necessary?
Get a can of Evercoat Formula 44 (West Marine). It's a polyester putty that's very easy to work with. After it's filled and sanded flush, you can leave it as is (it's a very light gray) or spray gel coat over it. On an old boat, with faded original gel, I'd leave it as is. You'll never match the color of your boat.
BradO wrote: 4) I have keyhole dogbones, with which end to you hook into the harness?
Either one. High one for lighter winds or big waves. Lower for heavy air / flat water.
BradO wrote: 5) I would like to remove the rudders for a long trailer ride. It looks like you just remove the two bolts on each rudder. My questions is, when I do this what will fall out? What more needs to be removed in order to trailer safely?
Easier just to remove the aluminum pins from the gudgeons. Everything comes off in one big piece.
BradO wrote: 6) How do you set the shroud tension. From what I have read it seems that you do not want to have too much forward mast rake. Where do I set this to get good a reasonable first guess?
Whole books have been written about this topic and there are many variables to consider. Do a search of this forum for more answers. Rig tension is set with the jib halyard.
BradO wrote: 7) My sails have number 356 on them. Are they antiques? 
Possibly. Depends on if there are missing numbers and/or those are the original sails.
BradO wrote: Thanks in advance for all your help,
-Brad
I live abour 30 minutes away from you, Brad and I've raced Hobie 16's for 35 years. Let me know if you'd like me to take a look at your boat for you to help you get started.
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