Here's the latest:
FIL suggested I use a chisel in the cavities, which I can do at home. I managed to carve one out already and glue a patch (not shown). He build a jig (in five seconds) so we could clamp the neck down without any movement. He has great ideas and a ton of clamps. The block of wood is for the Wangstang. As you can see, it's two pieces glued together, but in person it almost looks like one.
The headstock was stained such that I didn't even know it had a grain pattern. I got really lucky with the new tip because the grain actually lines up in a few spots. If I wanted to, I could try painting the wood grain by hand, but I don't think I will need to. The front of the headstock will be painted, and the back was not as dark. It should not be that big an issue. I have dealt with worse. Had I been smart, I could have tried to match the tuner plugs up better. One of them happened to land right. But they will be drilled and covered anyway, so it doesn't matter. Just a satisfaction thing.
Robert, the guard is yours, buddy. Maybe you can use it to make a template and spares.