if your working on a Chevy use the Chevy techniques, if not, don't
As far as using silicone on both sides of any gasket is a big NO NO in my opinion
I would buy a decent gasket sealer adhesive like Gasacinch to hold the side gaskets in place on the block and a tiny dab of adhesive silicone sealer, not gasket maker silicone, in each of the four corners where the oil pan gaskets meet the rear main cap and the timing cover up front. I do coat both sides of the gasket with the sealer and let it dry to seal both sides before installing the gasket on the block
Then install the oil pan with all the bolts in place and slowly tighten them up evenly on both sides until the bolts start to get snug, once that is done use the factory torque specs on the bolts three or four times letting the gasket set for 5 to 10 minutes between each tightening
IHTHs