Some folks online say it's best to start with a small bit and then do gradually larger bits to help avoid cracking gelcoat. Would you agree with that?

I saw a guy say that a countersink is less likely to "bounce around" than a drill bit so he uses that for the back burn to get it started. It seems like some people recommended using the countersink or a larger bit to create a beveled edge around the hole after the hole is drilled then using 3m 5200 on the hole before putting the screw in. Apparently the beveled edge around the hole is less likely to crack when something is tightened down on it than a flat edge.

I have no experience at all and have just been watching a lot of youtube videos. I'm planning to install a bimini on my mako 17 pro skiff (which is my first boat) tomorrow morning. Hopefully all goes well.