No need to drill holes unless its on a bridge, then maybe one, and size wont be an issue so longs as its smaller then the bridge width thats covering it, try one of the bits you use for pop rivetts the stumpy ones
but you should only need to put drill tip dimples down both side of the piston either side of the ex hole to hold some oil to bring up with it from the charge. i drill 4 dimples down both side, soime time if im in the mood nd feeling a bit crazy i drill them all over the place, be the funniest piston someone would see if they pulled it out . hehehe. but then again never seized a piston on the hot side ever, even on the superlight racer thats 13,000 or more revs on a 100cc air cooled so it must of worked