OK - I have been derailed by work and a bunch of other stuff so I haven't put anything about my 23 here for a while. I got a little bit done on the motor and got to work on the outside of the transom. Decided to raise the outdrive 2" from the original hole - instant opportunity for patching. Since I am trying to use gelcoat instead of paint I had to pay the extra work price. I used some VE to lay-up a layer of glass and used epoxy to put into place in the old drive hole; it is a tie bond layer so that I could use VE for fairing the hole and gelcoat on top of that.
Sanded it smooth except the part that will be cut out for the drive and sprayed it with some gelcoat - took a chance on color matching and lost, but it was good practice. I probably should not have masked it with tape but since the color didn't match I had to sand a lot anyways. I have never sprayed gelcoat before so this is a big time learning experience and I see that red isn't very forgiving.
Sanded it down and used a drill fixture to mark the cuts for the drive and drill the bolt holes.
Forgot to take a pic of the final sanded transom but it will get some more gelcoat on it before I do the final drive hole cutout - hope I get a better gelcoat match next time. The final coat will be over the whole transom so that if it isn't a perfect match (likely) it won't be so obvious.