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So I've slipped and ruined one to many holders and Its driving me nuts i even cut my thumb with the drill, I can't seem to get a centered hole either. what can I do to improve this?

Take the tip of a new blade and centre it on the end of the barrel. Once you're happy with its location you can level it out so it's parallel with the weapon/barrel and spin it a bit to make the hole slightly bigger. Once that's done, just use your drill as normal.

The key is to not go overboard spinning your blade (that description sounds terrible, haha) but rather make it act as a sort of pilot hole for your drill. Works every time

Hope that helps!

I just use a sharp knife to mark a spot in the end of the barrel. Twist the knife around until it makes a conical hole, then use an electric drill and go slowly.

ETA: Twist the knife a couple of times first, then look carefully at the hole. It will be off-center. Turn the blade so the sharp edge is toward the "meatier" side of the barrel, then repeat, adjusting every couple of twists. Eventually the conical hole will be spot on.

I use a small drill as a pilot then a larger one that way it doesn’t split, I also drill at an angle if it’s off centre to straighten it

I take it your not drilling eyes and want to know how to paint them?

You are using a hand held manual pin vise right? Use a appropriate size drill and center it, if slight off center after a couple spins- use a slightly larger drill bit and cover the mishap.

Eyes: paint the skin tone first, use a thin tip detail brush and apply a black dot in the iris, then a white dot on top leaving a thin line around the eyes, then dot the middle and clean up around any mishap around the eyes with skin tone.

For the likes of bolter barrels or otherwise flat-ended small area sections - use your knife to draw a line across the centre, then rotate and repeat so you have an X across the gun barrel. Don't need to go super deep, just a light line, the centre of the X will hold the tip of the drillbit enough to get started, and any spray undercoat or painting will fill in the score with ease.

As the above posters say, you need a pilot hole where the pointy part of your drill bit can "lock" on to.

Yeah, pilot hole. I use a spiky instrument from a manicure kit (not really sure what the intended purpose is), to make a guide hole. If i am drilling a hole any bigger than 2mm, ill then drill with a 1mm drill bit before moving up sizes.

For smaller barrels (like bolters), I don't even use the pin-vise anymore. I just use the same knife I'd use for the pilot hole and twist it back and forth until it gets the diameter I want.
When I paint the model, I just paint the hole black and it look fine.

But for bigger barrels, I still start with the pilot hole and them use the pin-vise/drill bit

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Like everyone's already said, the key part is the pilot hole. I'd recommend using an awl or another sharp, pointy object, though. Hold the weapon/barrel firmly and place the awl right in its center. Be patient at this point - don't apply any pressure until you're 100% sure you're happy with where it is. Then rotate it a bit and press it into the plastic. it's really the making of the pilot hole where you need to take your time - if that's where it needs to be, drilling the actual barrel hole isn't much of a problem anymore, although you should definitely take that nice and slow as well.

Also, have something handy to sand the end of the barrel afterwards to make it look nice and smooth.