The black plastic piece is to keep the daggerboard from dropping clear through the slot. I've installed one where it was already totally absent. In comes in two pieces that you have to pound together once it's on the board, so I think you'll have to drill it out. If you order your replacement part now, you'll see what I mean.
The stopper is actually three pieces, two end caps, and a center rod - the two caps are pressed on from each side, riding over small ridges in the center rod to stay in place.
You can usually pry an end cap off with two flat blade screw drivers (work them under the cap opposite each other), or you tap/bang on the center rod with something that has a large flat surface area (ie the handle end of a screwdriver...)
For your splits in the board, some epoxy resin will easily glue it back together.
My old wooden daggerboard does not have the part with the end caps and the center rod... I have never taken it off, but I can see the head of a screw on one side. I tried to take this out and it was badly bent. The hole is a lot smaller also. If you buy the "modern" replacement, you will have to drill.
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