Working on the transom

It seems like a bad idea to put holes in the transom, but that is what needs to be done.  There are two holes above the waterline that empty the motor well.  I am also emptying the bilge pumps into the motor well, so there needs to be drain holes.
In addition, there are drain holes that empty the bilge. These are a little scary since you are drilling holes below the waterline.  If these leak or the plugs fail, you are taking on water big time.  I even debated whether to add these or not.  However, most plans and most builders put these in to permit draining the bilge when the boat is on a lift or trailer.
To cut these, I used a 1" Milwaukee hole saw.  I wanted to make sure the holes looked symmetrical from the transom side so I actually measured the points and marked them on the outside. I figured they make be a little off on the inside but they would look right from the outside.  If I started from the inside and my drill orientation was a little off the holes would come through at different points.

Here's the drill making one of the motor well drain holes.

Here are the two bilge drains.  I inserted the brass drain tube to show what it will look like. It is not epoxied in at this time.  These two drain tubes will have rubber plugs to seal the hole and make it water tight.

I also drilled holes for the two eyes that are attached through the transom. These are used to tow water skiers and also used to hold the boat to the trailer when on the highway. These are through bolted through the transom with an extra white oak backing plate on the inside to add some beef in this area as seem below.

Another challenge was squaring the transom.  I used a saber saw to cut down the transom to the desired 20" height for most modern outboards. However, when complete, the cut is not square to the transom or completely straight.  To clean it up, I squared up some 2x6 lumber and clamped them to the transom. I used this as a guide for the angle grinder and belt sander to level it up and square it.

 After the cut out was cleaned up, I glued some mahogany veneer to the top of the transom to make it look better. The edge grain of the plywood just didn't look right.  Unfortunately, I had to buy a 1x8' piece of veneer for a 3"x36" section.  Oh well, it looks good.