just my opinion, if your drill bit is nice and sharp (i.e. not dull with high-mileage) and good quality, then, if your feed rate is really slow, the drill swarf (chips) should be pretty small and easy to break off, leaving a nice clean transition at the edge of the gas port hole in the bore.
check the alignment by sticking the drill bit of the existing size in the barrel gas port, and the prospective drill bit in the chuck, bring them down next to each other, and make sure they're parallel to each other from from all angles.
those aluminum barrel vise blocks in an x-y cross vise help. i wouldn't do this without a drill press. and be sure to calculate the percentage increase in port cross-sectional area that you're shooting for, as a minimum calculation, when figuring out how much more to go.