I'm new here also, but let me share something I've learned.
First use either MS Word or OpenOffice Writer. Load you txt file in and give it a title. Select it and give it an h1 or heading 1 style. Mark each Chapter with a number and/or title. Give all these an h2 or heading 2 style. Save this file as an RTF file. In Calibre, read in the file. Choose "convert individual file". In the next dialog box select "Chapter Detection" If you have more than 50 chapters, increase the default. If you have less than 6 chapters, decrease the limit. Now, in "Level 1 TOC use "//h1". Thats for the title. IN Level2 TOC use "//h2" (don't use the quote marks!) That's all there is to it. I had troubles too, and they didn't go away till I used those simple xpath statements. There's lots more to that you can add, but you'll learn this as you go.
HTH
Paul
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