Where are you buying your starters? There are some starters that people are selling that are real crap. Do not buy a $50.00 starter from EBay, I bought one, it wouldn't even work right out of the box.
Lou
There is no connection from the water jackets in the engine, and the starter. So... there is no way that is happening. Now... the starter is on the bottom of the engine, and even a couple inches of water will submerge the starter. If you buy a new starter... before the install... take it apart, and make sure all the seals are good, and assemble it with a little RTV.
if the bailer tubes are not hooked up, at the pump (on top) / missing tubes inside the pump assy, then, the bailer system will work in a reverse effect, causing them to syphon water INTO the hull.
Made sure the o-ring was with the starter? Aint those starters a PITA to get to/install....:willy_nilly: