I have been tempted to do the same.
A drain hole solves the problem nicely for those of us who haul every winter. Any photos or descriptions of this addition? I am a bit worried about the potential for leakage, but as long as it is installed properly it shouldn't be a big deal.I added a bilge drain hole on my Catalina 30 at the lowest drain point with a pipe threaded plug on the outside. At the end of each season I add a detergent to the bilge a few weeks before haulout. When its high and dry, I totally drain the bilge and pressure wash it a few times. The winter cold dry's the bilge nicely. Any rainwater/ snow melt that gets into the boat finds its way down to the bilge and the exit hole. However, you must remember to put the pipe plug back in the hole before launching in the spring.