I did a quick inspection grind last night to see if the aft part of the keel was indeed fiberglass or built up with some other material. It is indeed glass all the way back and the grey material I really believe is gelcoat. It was the same thickness/consistancy as other areas I have grinded on this boat. The four pin holes show that the area has been wet for some time as there is discoloration around each of them. I'm sure water entered the laminate where the discoloration is, but the integrity of the area I don't believe is compromised. I plan on grinding out with a dremel all of the rotten area (I feel like a dentist), then letting the area dry for a while before filling the ground out areas with epoxy.

Interestingly enough the dripping from the shoe area had stopped last night and I vacuumed my bilge so that it was completely dry. Then I drilled the four pin holes with a drill bit twice the diameter of the original holes to gauge how soft the area was. It seemed solid except for where the bit travelled through the discolored glass which was to be expected. When I went to work this morning I noticed some water had leaked through and frozen last night. I think drilling those holes helped the water escape faster and that grinding out the discolored glass will help dry the laminate out even faster. Ultimate goal: no water entering or leaving my hull from anywhere unless I tell it too.