First of all, did you get all the old gasket materials off the surface of the timing cover and clean it well? Be sure you didn't distort of fold the gasket.
Don't double gasket. Only one gasket by itself. No need to use silicone and the gasket, that causes more problems than not. If you want to use something to make it stick, there are products for this. Some like to use a little adhesive such as 3M Weatherstrip Adheasive a.k.a. "gorrilla snot". I perfer to use the spray on type.
Silicone will work but sometimes it needs time to settle especailly with water. I like grey better than black. You should use a little on the bolts to seal the treads.
Weather silicone or gasket, don't overtorque. You want to tighten them to just past snug. Hold the bottom of the rachet/wrench so your thumb is on/near the bolt and turn it with a firm tug, not hard, just firm, such as when you are turning off the garden hose. Also, tighten from one side to the other, such as the star pattern when bolting on a wheel. Perferably in steps. At first hand tight all the way around, then firm, then finally just past firm.
I turn wrenches for a living, change a lot of waterpumps and such, rarley have to go in twice, but sometimes it does happen.