What tool are you using right now to author in & make PDFs from? RH can use FrameMaker or Word as sources for linked content.
We’re using Word. FrameMaker may be in the future.
You could import all the Word documents into RoboHelp and then edit there. Your printed output could be generated from RoboHelp.
You could link to the Word documents and generate both online help and printed documentation.
RoboHelp has multi level lists that work within a topic and you can autonumber images (figures). Cross references can be converted to hyperlinks, that is covered in the Importing pages on my site.
The unknown is the complexity of your Word documents and how well the import / link would handle that. You would have to download the RoboHelp trial and see how it goes. The problem then would be that you will need a reasonable level of knowledge of RoboHelp but you will be beginners. This will apply to other help software. As a moderator of the forums I can see your email address and from that I can guess your location. I do know there is a RoboHelp expert in your area who would be able to advise on likely issues. That would be paid consultancy. If it is of interest to you, contact me via my site and I will put you in touch with him.
I suspect that if your documents were in FrameMaker, there would be some advantage but then you would have two tools to learn as well as how they play with each other.
I hope that helps you a little.
See www.grainge.org for RoboHelp and Authoring tips