The rivet gun that we sell here has the two handles ($32) and it's the only way to go for popping stainless rivets. As you found out, if you into sailing for the long run, it's dough well spent to just get the bigger gun. The $89 gun that I use is nice, but the $32 gun does just fine. The $20 gun doesn't.
Mast cleats can be a problem, the hole pattern on the old cleats doesn't line up with the holes on the new ones, and they're usually too deep for the nose piece of the rivet gun to properly seat the rivet.
If you have to drill a new hole, I've seen people use JB weld or silicone to seal up the old hole. I've used a rivet with a cap to seal a drilled hole in the mast with good results.
Here's what to do:
1) Get a better rivet gun.
2) Get the holes lined up.
3) Place rivet caps in the holes with a little silicone on them to seal them up well.
4) Place the cleat with the rivets onto the mast
5) Make sure the rivets are seated into the cleat. Use a pair of plyers and 'snap' the rivet body onto the seat of the cleat.
6) To make the nosepiece of the gun seat properly on the rivets, use some small washers and place them onto the mandrel. Use 3 or 4.
7) Pop the rivets
What the heck is a 'murray cleat'?
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Hope this helps!