So after struggling to get the starter to work and then the engine to idle everything seemed happy on the muff so I put the boat in the water. Yes, I had the drain plug in 
Was pulling the boys around on the tube for about an hour and then all the sudden the engine started sputtering an died. I went back to look at the engine and saw a water up to the starter. I flipped the bilge pump on but it could not keep up. got a tow to shore.
Pulled boat out figuring somehow the drain plug had release itself. No, it was still in tact but water was coming out from the stern drive area. I'm guessing somebody on here already know without the pics what happened but I'll include pics anyway.
One from left side prior to pulling drain plug, one from right after pulling drain plug.
Was pulling the boys around on the tube for about an hour and then all the sudden the engine started sputtering an died. I went back to look at the engine and saw a water up to the starter. I flipped the bilge pump on but it could not keep up. got a tow to shore.
Pulled boat out figuring somehow the drain plug had release itself. No, it was still in tact but water was coming out from the stern drive area. I'm guessing somebody on here already know without the pics what happened but I'll include pics anyway.
One from left side prior to pulling drain plug, one from right after pulling drain plug.