First of all, it is called an eye strap and not a strap eye. First of all check to see if the fasteners have nuts on them or are just screws. If just screws, then just unscrew them. If through bolted, that you have to find your way to the underside and if something covers the nuts up, you have to somehow cut a hole through whatever material it is to obtain access. Often in that area there might be foam for flotation. If you can see stains from where it leaks below, then I'd think you should find the nuts. The winch, as mentioned above can be disassembled, the drum removed and then the bolt heads will be exposed and you will need access to them to refasten the winch after caulking. To break what seal you have, you can take a chisel or flat screwdriver and gently tap between the deck and winch base to break the seal. If your Macgregor (not O'day as mentioned above) is not the trailer, then your stress of losing parts is lessened. If the boat is in the water, having using the shoe box method is a good idea, or have someone else around to help keep things in place while you remove the winch. Once the winch is apart, it is a good time to clean and put new grease on the bearings. It's an easy job for your winch types as you will find out. Just use the right grease designed for that purpose. Something from Harken or Lewmar works (West Marine has admitted the winch grease they sell isn't the best - or at least that is what one of their reps admitted).
