What's critical is if you are drilling aluminum vs steel! A drill bit in steel almost *always" wanders some. That is even if it is in a drill press; unless you chuck the bit "up" in the chuck and end up with a very short length of drill below the jaws of the chuck.
DEFINITELY recommend a pilot hole whether alum or steel. Absolutely. Give yourself every advantage you can. Yes, there is a drill bit looking tip on a step bit but they tend to be....not so good.
What I would do: "rehearse" a practice hole in a piece of scrap, if you can. Do a few of them until you feel comfortable.
STOP drilling the hole you drill in your real chassis short of its final size. With a knife or a file, get rid of the burr both on the top and the bottom that the step drill will create.
See if you can stop with the step drill just a tad short of final size and finish off with a rat tail file. If the flange of the socket is to be mounted on top of the chassis, you can be a little more aggressive with your drilling, as it will be covered. But if the socket mounts from underneath, try to finish with a rat tail file. It helps to have a BIG rat tail file. Most people have little (less than 1/4" in diameter one) but a larger one will make your life easier.
You shouldn't have a problem with an intersecting hole, if it's not too large. Especially w/your drill press. But...it is not necessarily the easiest thing to clamp a chassis without bending it, either.
Again, give yourself every advantage you can: Drill a pilot hole, file off the burrs before you reach the final size of your hole(s).