I was a mechanic in a very large utility fleet. I probably changed a couple water pumps a month for the past 30 years. You won't have this problem on your flathead but on a lot of engines your trying to slip the pump and gasket in behind a bunch of other brackets. Usually it is such a tight fit that you run the risk of accidentally catching the edge of a gasket and folding it over, resulting in a massive leak. You need to glue the gasket to the pump so it will not move. Using silicone on both sides of the gasket is a bad idea because when the silicone squeezes out during the tightening process the gasket can squeeze out along with the silicone.
Gasgacinch is my favorite gasket sealer. This is a contact cement that you brush on, it remains slightly sticky so if you need to lift up the gasket and reposition it you can, and if you need to scrape off the gasket years later you won't destroy the part trying to get the old gasket off.
On a water pump installation I will use Gasgacinch to glue the gasket to the new machined surface of the water pump. I brush on the Gasgancinch on the water pump and the water pump side of the gasket. I let the glue dry on both parts until it is slightly sticky, then I position the gasket on the part and it is not going anywhere.
If the machined surface on the block is real nice you can use Gasgacinch on that side too. If the block has a lot of scratches from the careless use of gasket scrapers then I will use a little bit of silicone instead of the Gasgacinch on this side. The silicone fills in those little scratches which can act like little channels for the coolant which can cause seepage problems. Were not talking about running a caulking gun bead of silicone, just a little 1/8 inch bead. Keep it away from little oiling holes or coolant passages that can become accidentally plugged.
The high heat red silicone is the best silicone to use but on my cars I don’t like seeing red, orange or blue silicone oozing out of my engines. I use the Permatex black silicone which works real well and is not visible when I'm done. Just make sure you get the black silicone made for engine gaskets and not the type for sealing glass.
Gasgacinch is especially useful for gluing intake gaskets to heads when you want to make sure the gaskets stay lined up with the ports. Buy the smallest can they make because once its opened it goes bad in about 6 months.