Newbie dumb question #1 : wet bilge

[Salty19]

Jackrabbit--You might be overthinking things a bit.

Wes is right, the mast step is designed that way on purpose.  Unless the wood under the step is waterlogged, which would require a repair, just screw the step in with a good sealant and don't worry about it. If any do not tighten (ie spin freely) then let us know.  I've never seen a report of the mast step ever breaking on a CP19, and I've been here on forum for a good 10 years now.   I've seen reports of them bending when rigging failed and the mast came down, or when raising/lowering the mast and the mast sways too far to one side (in cross winds the mast can be hard to control).

As far as oil canning, I will venture a guess to say your boat has been on the trailer a long time, perhaps tied down aft with a tight ratcheting strap and formed a new shape.  During this time it has moved a bit, like all fiberglass structures will tend to do under tension.   The new shape will work itself back out to where it originally was given some time off the trailer and in the water-perhaps a few weeks or so.  During this time, your rigging tension is going to change--probably get tighter.  With this said, once you splash the boat, set the rigging to sail it, but then keep loosening the turnbuckles a little bit each time you leave the dock for the day (I presume you are using a mooring or slip) until you feel the movement of the glass has ceased.  This will avoid too much tension on the stays and rigging during the time the shape is moving back.  This is especially important to prevent the fiberglass around the chainplates to keep from cracking under high stress.   

If you add fiberglass now, it's going to stay in the incorrect shape.    No need to add more, these are strong boats and your problem is likely from a lack of being in it's natural position (sitting in the water). You would only be adding weight and as mentioned could lock in the ill-formed shape if you add any glass now.

Ahh, the details of sailboat ownership!

[Jackrabbit]

Amen!  But I wouldn't have it any other way. 

I do love this boat.  Now we are planning a week-long cruise in the last week of July, waffling between the North channel (a long drive from my home near Ottawa, Ontario) and a circumnavigation of Prince Edward County (that big peninsula that juts out from the Canadian shore at the Eastern end of lake Ontario).   Adventure in big waters!

In any event, a week of sitting in water ought to do her hull shape a world of good!