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that split finger nail looks like a bugger!
I always do the bolt holes first. I insert the bolts to hold the gasket material in place. If possible, I put the part in a vise to hold it firmly while tapping. I also use a much smaller ball pean hammer. It fits the inside curve easier.
This is nothing new, Mechanics in the army have been doing this for over 100 years now. I had done it myself when I was fifteen years old when I needed to make a thermostat housing gasket for my mom's 1968 Buick Skylark when I had replaced the thermostat and I used an old manila folder from school for it.
Funny how things change. When I was a young guy the headers I installed on my new "68 SS 396 constantly leaked. We made a gasket that permanently sealed the leaks, but we used .asbestos. It was great stuff back then.
my father showed me this in the 1960's
te hammer gasket Guy did it WRONG!--the Water out let should be the First thing You DO!--as by Doing the out side--the Gasket often turns a bit--thus--poor Gasket--
Once you hammer out the bolt holes, drop some bolts into the holes to hold the gasket in place,