Help generating TOC

Hello forums. This is my first post here.

I just downloaded Calibre tonight. I've had a Kindle since the first one came out and generally just haven't done much but read books.

I need help generating a Table of Contents for a book that my brother-in-law is in the process of writing. I can't figure out how to make an XPath expression that will find the proper phrasing and generate a table of contents.

He's decided his chapters won't be like "Chapter Two", etc.

The denotion of a chapter will be a single word in BOLD CAPITAL letters for the geographic location of that chapter.

For instance:

DALLAS

TAMPA

LONDON

The only places in his book that will have all bold capital letters will be the chapter headings.

Calibre has located his more obvious items such as Prologue and Epilogue, which by the way also happen to be in BOLD CAPTIAL letters. I guess it just looks for those types of words automatically.

Can anyone help me figure out how to help my bro in law not only generate a table of contents, but just start a chapter on a new page? Right now the chapters all run together. You can see the BOLD CAPITAL geography and tell that you are in a new chapter, but otherwise you'd never know. The last sentence of the previous chapter is one line above DALLAS.

Can Calibre help me find those BOLD CAPITAL letters, insert a page break and generate a TOC or do I need to find some way to do this manually or use a different program or whatnot?

Any help is very much appreciated.

The source material he's given me is a PDF.

Thanks in advance.

Carl