I like to modify my guitars, I apply my finish to my guitars. Does it make it wrong? My guitars still make a sound just the same as everyone else's, my finishes are just as shiny and I use a lot less to obtain said finish, just the way I get there is different, I just like to think outside the box.
Everyone has their own idea about the keyhole design, while some are saying they like it, some cannot fathom why? As with everything in design try and break it down, and all will make sense and you will find it just doesn't matter.
Through body strings are a personal choice, I like them and I convert all the guitars I build to the system even though some guitars I buy are of a Gibson design that uses a stop piece. I convert to a string through as I like the way they look and for the, in my mind, string stability they offer as there is a definite stop and unless the wood shrinks or expands the ferrules never move.
As for the keyhole design you just have to look at it as a different way to get the string from the back to the front and how to remove the wood from between the ferrule and the hole in the bridge. You can drill a hole the same size as the large round area of the keyhole and leave it as it is. Depending on the wood used in the body will determine how much the wood will deform under the strings tension and what effect that will have on the string. At worst it may deform on softer woods and you will have to retune your guitar until the wood wears away completely and the string then rests upon the end on the smaller slot and on harder woods it may never move. How does it look leaving the wood there? Some people may think it doesn't look as good if it was removed but when I play my guitars I don't really notice anything other than where my fingers are going on the frets. My thoughts on guitars are they are for playing, not displaying. If I want to display something I put a painting on the wall.
You can drill a hole and then use a small round file and remove the wood at an angle to the slot so as it mirrors the strings angle that exists where the string leaves the ferrule and sits against the slot of the keyhole. More work but it would look neat but again I don't care as I wouldn't be looking. If you want it to look neat then you do you.
My plan of attack, if I was to use a bridge with a keyhole, would be to drill a hole that was big enough to remove all the wood under the keyhole. How would you know where to drill said hole, I hear you ask, easy I reply. Fix the bridge to the body via the screws, mark the end of the slot and the opposite side of the large round hole, which is parallel to the string and along the same axis. Then mark the sides of the large round hole. Do this to all the slots and that will give you the position of the hole.
Remove the bridge and run a line along the ends of the slots and the end of the round hole. Find the centre between the lines and that gives you the centre of the drill hole. The size of the drill is the distance between the 2 lines, you could even go half a millimetre, would not make a bit of difference as the string will still contact the same parts of the bridge and ferrule. Now find the centre between the marks made by the sides of the round hole and that is the exact centre where you will drill your holes. Don't drill all the way through as you need to drill the rear face to fit your ferrules. How you do that is up to you as you have to work with what equipment you have. That is as simple as it gets.
Break down what is being discussed and what is needed. The ferrule is positioned on the back and is stopped from being pulled through the body via the lip on the head of the ferrule and the string passes through the small hole on its way to the bridge where it contacts the small slot end in the keyhole. It then goes to the part of the bridge that adjusts to give intonation and string height. Everything from the ferrule to the saddle is irrelevant as the important part is from the saddle to the nut. The break angle, no matter whether you remove the wood or leave the wood, is sufficient to make the guitar make a sound and makes no effect on whether the guitar will make a sound or not.
My work here is done