Being the impatient type I am, I got going on this project w/ your little push.
Removing the nail(s) was fairly simple. Underneath them, not so good. beside the hole, a crack follows down the checkering about 1.5". You can barely see it just below the bottom hole. I can repair that w/ CYA. Like you say though, the checkering could prove challenging. Yikes, I don't have tools for that...
Should I try & remove the surrounding wood around the hole or just fill it up w/ epoxy?
I removed all the Ebony because it seemed like the right thing to do. I have some ebony from my guitar making that will be used. Patching it nicely will test me.
Watch the magic @ the 6 min mark on the YT Vid: