[Knot On Call]

While underway this season I noticed that my keel pump would turn on approximately 30 minutes into the trip and remain on for the trip. The keel pump would stop while at rest.  While underway, I went down into the aft bilge  through the trunk and was able to see the interior of the swim platform. I observed water entering along the seam between the swim platform top and hull at 3 different locations( aft port and starboard side, and center rear) falling into the bilge. The center rear location was actually cascading water to the bilge.  I would like to seal the entire molding area and would like to know the best way to do that to stop water intrusion.  After talking with Brian at Tiara I removed the SS edging and molding around the swim platform. 
When I removed the molding to reseal the platform, I noticed that the molding, as installed was covering the drain holes of the roller housing and that some of the drain holes (arrows) on the roller frame were sealed with caulk preventing the water from draining out.  You can see the original height of where the molding was installed over the drain holes. (pictures are included)
My concern is the boat runs at altitude with the water stream right along the molding just below the rollers. The rollers are  continuously splashed and as the boat runs, water may be being pushed under great pressure into the roller holder and getting behind the molding through the drain holes and running behind the molding and along the inside seam of the top and hull finding its way in to the boat. Most of the water is entering the boat from the swim platform area, aft mid-ships right along the seam.  Water stains are also present on the inside hull shell in the area of both roller housings. 
Tiara couldn't provide tech help when I asked  why were the drain holes plugged and covered with the molding. Seems like a bad designed me unless the molding reduces drag spray from the rollers. Said all boats were built that way but couldn't provide a path forward for how to reinstall the molding- below or over the drain holes. No records or anyone to talk to.  If I reinstall the molding below the drain holes I will have to notch it out around the roller housing which would look bad. Any suggestions?
Thanks for anyones' help.