1) Sealing the bottoms of the screw holes for the plates that hold the wedges. I did not put much sealant on the screws in case removal was required down the road. Water weeped from these holes for 2 weeks.
2) Using a temporary spacer between the CB and the wedges until sealant cures and not a lot of sealant on the wedge in case you have to remove the CB again. A small amount of sealant will keep the wedges from rattling.
3) Smoothing the groove the original cable cut into the CB trunk where the halyard tube is attached in the CB well. Some of these have cut all the way through causing a leak at this junction. This is probably the cause of most problems after someone changes the halyard to line that is larger than the original cable diameter.
4) If you are going to use line instead of cable for the halyard (I recommend line) line the halyard tube with Pex tubing for a smoother running halyard. It's tricky but you can seal the Pex tubing where it comes into the top of the CB well with 5200 to eliminate leaks in the old FG tube.
5) Redesign the halyard to CB attachment so the line does not have a knot on the trailing edge of CB to catch in the tube at full up. This is done by carefully drilling a hole into the trailing edge along the axis of the CB. At about 3" from trailing edge drill a 3/4" hole from side to side. Feed the line through the trailing edge and tie a knot that can rest inside the 3/4" hole. Seal holes with sealant that can be removed.
6) Before painting or barrier coating the CB, trial fit and check for clearance inside the well. Some wells have collapsed slightly and you may have to remove some CB fiberglass to get enough clearance.
7) If the CB swing pin is a tight fit open the hole or sand the pin. You want a little free play to eliminate some of the problems in number 6
After 18 months of sailing at least once a week a small child can pull up the CB, my halyard has no wear (yet) and the bilge is dry.