Tool for building a reference guide website or document generator?

It's certainly possible but whether it's $50k or not will mostly depend on the complexity of the logic for toggling parts of your word processor files (your "complex user inputs"), and whether you want a generic solution that processes arbitrary legal documents or if you just want one for incorporation and bylaws. Without knowing the detail of those features, or how many legal documents are involved in "bylaws" it's difficult to say whether your budget is appropriate or not. I've written a few legal document generators over the years (I wrote http://github.com/holloway/docvert to process office files) and typically people script a server (headless) version of LibreOffice. The reason for this is because you can't use Microsoft Office programmatically for a CAL-less user without violating the EULA. The basic architecture is that most people dynamically generate OpenDocument files based on answers to a web form (in Drupal or anything) and then script LibreOffice (via UNO in Python or Java) to export PDFs or Word files. The good thing about using a word processor format like OpenDocument (as opposed to XSL-FO or another lower-level PDF generator) is that you get the formatting you'd expect from a word processor, with TOC , line number references, bookmarks, and so on. It sounds like you need to write an RFP to see whether your budget is realistic or not.

Oh sorry, a clarification: in this ideal setup, there would be no Word Docs involved anymore: the user would fill out a web form and download a PDF. On the backend, NPA staff would have some sort of content management system to update the legal text and move around variables.

I understand and I'm answering the bit about "tackle this with existing tools" by suggesting a basic software architecture. These types of legal document generators typically use word processor files (as an intermediate format) even if the user only sees PDFs. If you're just asking whether it's possible then yes there are many sites like LegalZoom.com and LawDepot.ca that do this. Drupal also has many PDF generators like http://drupal.org/project/views_pdf. It can be as simple as generating HTML if you have simple requirements. ...but ignore the PDF document generation for a second and it's like you're asking "I want to build a website with complex forms that make pages and I want to pay about $50k is that realistic?". That's just not enough information to go on... I'm not meaning to be harsh by saying that and I'm only meaning to convey that I don't know how we can answer your question without knowing how many documents, and how complex they are :)

I think the $50k is bit of a red herring, as I just threw that out there as an example of how much a custom web app could cost. They don't want to build a custom web app if they can avoid it. The actual budget of the client in question is much, much lower: under $10k, ideally under $5k. And I am the developer who would be possibly implementing the tool. I do Wordpress/Drupal theming and install, but I don't do custom web apps, so my question is an attempt to scope whether this project is within my skillset and the client's budget for my time. If they wanted a social networking site, for example, I'd set them up with BuddyPress and that'd be under $5k. But I've never made a thing like this, and I am having no luck looking in the places I usually look. So I'm not as much asking "is this website possible under $50k?" as "are there existing, open-source, well-documented tools to do this, or should I tell them I can't do it and they can't afford it?"

I think this is possible within their budget by creating a userform, which is a VBA form that displays in Word and the ultimate output would be Word. I do see you are not interested in Word, but that would keep it within their budget.

Yes TCPDF is used in the Drupal plugin I linked above. A PHP library for making PDFs isn't the difficult bit here unfortunately. @Houstonian they want something like a Drupal addon for the public to use.

Important to note that web standards support for styling of print are http://www.w3.org/TR/2013/WD-css3-page-20130314/ http://www.w3.org/TR/2013/NOTE-css-print-20130314/ right now as new CSS3 features are being added by the browser vendors from month to month. So, a solution could generate a web page that will print correctly in one specific browser (for starters, though being cross-browser would be ideal of course) and simply print to PDF. Though holloway probably has a better grasp of whether the specific requirements of generating legal documents would be met even by fully-implemented web standards. For "open-source, well-supported solutions" you probably couldn't do better than industry-standardized cross-vendor support of the print layout mechanism, similar to the benefits he describes for using a standardized open source word processor format. I'm just thinking that a completely web-based system, like an open source wiki that supports http://en.wikipedia.org/wiki/Wikipedia:Transclusion such as MediaWiki or http://jamwiki.org where you can break content down into arbitrarily small pieces and each one will have its own talk page, change history, access rights, etc., might be a better fit for some of the other requirements. (Overall, however, it might serve you best to put the majority of resources devoted to the project into nailing down and documenting a consistent workflow and procedures, as well as training for the MO personnel involving web videos and other reusable self-service materials, regardless of which technological solution you arrive at.)