Catalina smile?
When I was shopping for my boat (bought an O'Day 272) two years ago, I found a Catalina 27, about the same vintage as yours, which had a very small leak in the bilge. As I explored the leak, and then did lots of internet research, I came across a condition known as the "Catalina smile." Seems that the foundation under the keel bolt heads is plywood encased in epoxy, which is subjet to rot if water seeps up into the bilge due to loose keel bolts that might have been aggravated by a grounding or other bump to the keel. As the bedding under the keel bolt nuts in the bilge softens, the keel sags enough to create the "smile," a small opening between the front of the keel and the hull stub where it attaches. There are good references to this on the web if you just google "catalina smile." Fix seems to be to open up the bilge, remove epoxy cover, all wet plywood below, and rebuild. Not killer, but definitely a job to be done on the hard, not in the water. Good luck.