+5  A: 

Have you considered DocBook? You can render that as just about anything. See this Code Project article for examples for CHM generation.

Paul Dixon
No, so far we haven't looked at DocBook. We will do now, thank you.
sbi
+1  A: 

Check out Help And Manual http://helpandmanual.com/products_hm_features.html

Conrad
A: 

You could achieve what you want if you implement the following:

1) Generate Html from XML

2) Generate CHM from Html

You can use Microsoft Html Help workshop to generate CHM files using Html, see: http://www.microsoft.com/downloads/details.aspx?familyid=00535334-c8a6-452f-9aa0-d597d16580cc&displaylang=en

3) Generate PDF from Html using an Html-to-PDF tool.

Mark Redman
I'm afraid that PDF generated from HTML might be hard to layout nicely. The same goes for the other direction. That's why we were looking for a format from which to generate both of them.
sbi