Drilling straight down through the mast step will not work as it is solid FRP and aluminum. If the step has no debris in it, it should drain aft through the low area in the step. See the link below for a picture. It would be in this area where it would be best to drill a small hole in the aft section of the mast. A right angle adapter and a short bit would work with the mast up.
Re: mast bolted to step? [Re: Conundrum]-Chris