IMHO, do not drill the vent hole with the breechplug in the barrel. Remove the plug, make a punchmark where you want the hole, drill a pilot hole, then drill the proper sized hole for the threads of the vent liner.
Then with the barrel still clamped to the drill press, take the countersink bit & put it in the drill press & cut the bevel for the seat of the liner.
Then with the barrel still clamped to the drill press, remove bit & install tap into the drill chuck.
Now, TURN OFF POWER to the drill press...... Then hold slight down pressure on the press handle & turn the chuck with your other hand & start tapping it. Tap a lil, back it out, reoil, tap some more, back it out, etc. This way I know the hole & the threads are in straight.
Next clean all the metal shaving out of the hole & deburr the inside of the hole so the patch/jag will not catch or tear on it.
Install the vent liner just snug to check length & make any corrections necessary in the bore. Now take it back out for now.
Now make sure the breechplug threads are clean & put the plug back in almost all the way. Take center punch & mark your vent hole (thru the new vent liner hole) just a tad above the center as the plug is no in all the way.
Now remove the plug & make your relief in the plug face. Then put it back & check it to insure you have it right. If it is right take the plug back out & install the vent liner with a tad of antiseize on the threads. Now do the same with the breechplug & take it to the proper allignment.
Now put a couple of wraps of electrical tape before & after the vent plug lug. Now take a fine tooth hack saw & cut the lug off. Now remove the tape & file the vent liner flush to the barrel, filing parallel with the flat. I use a black marker on the flat & the liner & file, and I can see if I am hitting a bad place or whatever, file it nice & flat for about 2.5 to 3".
Now, the reasoning behind not drilling it all at one time. I have seen this happen several time.... Guys drill that hole & when it goes thru the barrel & when the bit hits the face of that breechplug, the face of the plug will force the bit over away from the face & that will elongate the hole. So you end up with a oblong hole & no threads on two sides of it, just like the photo.
This is NOT safe & should not occur. Should you have a hole like this you then have to drill to the next size vent & retap & etc.
PS: No, I didn't do this one, but I did redrill it & install the next size vent liner in this one......