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It would be lovely to select a style sheet as you are generating the output, wouldn't it? As far as I can see, however, style sheets are assigned per topic thru a reference RH sticks in the HTML header.
Which leaves you two options:
1) The simple but tedious way: In the Topics list (on the right), select all the topics. Right-click and pick Properties. When the Properties window opens, choose the stylesheet you want on the Appearance tab. Click OK. You would need to do this each time you switch from generating WebHelp to generating PDF.
2) The complex but cool if it works way: I don't use the PDF plug-in - do you still generate PDF from the Printed Documentation layout? If so, can you use the StyleMapping.dot template? (I seem to remember that the PDF goes through a Word stage behind the scenes.) You can open StyleMapping.dot in Word (be sure to use File > Open so you get the .dot) and change the styles into what is effectively a new style sheet. It may take some tweaking - I still can't get my bulleted styles to come out quite right - but it's great for global changes.
I can think of maybe an easier way.
Create your two style sheets. Call one PDF.CSS and the other WebHelp .CSS. Use a common name such as Styles.css that is actually used by the topics.
Prior to generating a .PDF, from Windows Explorer, copy PDF.CSS over Styles.CSS.
Prior to generating WebHelp, from Windows Explorer, copy WebHelp.CSS over Styles.CSS.
Hope this helps a bit... Rick