Thanks for the suggestions....I'll try them out this weekend.
With regards to the speedo tube - - where does it enter the transom? The external portion runs into the drive in the same area as the bellows, but I was looking tonight and couldn't see a similar hose (as is attached to the pick-up) coming into the engine compartment. I know it has to be somewhere within the transom plate, but didn't see it.

If you have a low sitting boat like my Fountain, check the rub rail. I would get water into my bilge and couldn't figure out where it was coming from. It ended up being that it was getting in everytime I come on and off plane. My rub rail sits low near the water and would go under water coming on and off plane. I removed the rub rail and found exposed holes from a previous rub rail replacement. I filled those holes. Also, run a bead of caulk under the seam where the two halves of the boat join, under the rub rail. I did this and on my particular boat, solved the problem.