Okay good, thanks for the pictures. They clarify a lot.
I thought you had written the compression post was made of wood. Your pictures show the original gold anodized compression post. It has moved, been moved, from its original position. I suggested your boat had been the victim of a hard grounding. That is still a possibility, but it looks more, to me, like the previous owner was in the habit of over-tightening the stays and they, along with various shocks over time, have damaged the boat he may have moved the post so it doesn't sit directly on the crack anymore, but failed to fix it or compensate. There may also, very likely, be rot in the supporting structures under the tabernacle step. These things need to be fixed.
The aft rake of your mast is normal, but probably more than usual because of the mast's shortened height. Fix the crack in the bilge, fix the cabin top and replace the compression post to its original location and your other issues may resolve themselves.
-Will