wow, 1900
Man, seriously, this may seem like it could be fun,but i really urge you to get this repaired professionally.
When i was given a tour around Merton college, where they do a gutiar building course (I got accepted! WOO!), they said that it would be about 6 months before they even started to tell us how to fix holes, and then they were perfectly square, and they had the bit that came out of the hole.
Im worried that you may be going in far far to way in over your head.
I would never try to discourage you, and im sure that if you put your head to it, and practiced on many more hole repairs first, MANY more, then i wouldnt touch a guitar that is one hundred years old, its a piece of history, i would seriously look into having it repaired professionally.
Anyway, if you choose to do this yourself, i believe you are going to need all the help you can get.
Good luck.
Edit: Sorry, it seems like im being mean, and saying that your skills arent upto this. Im sorry if this seems offencive, but its just what i feel. I wish you the best of luck in whatever you decide to do.
Matt