Bad Word docs make for bad HTML (Score 1)

The tool you use to convert Word docs to other formats (HTML and PDF included) is, for the most part, irrelevant if those Word docs lack internal structure (semantic information), which in Word comes in the form of paragraph styles. These paragraph styles are analogous to HTML tags, like h, p, li, and so on. Unfortunately, most people who use Word are oblivious to the existence of these styles. In the typical Word doc, all paragraphs are just "Normal" with a ton of inline formatting; headings may look like headings (bigger font, bold) but they don't have a heading style. The structure of these docs is, thus, hidden from screen readers. Garbage in, garbage out.

Actually, converting semantic Word docs to other formats isn't very difficult; the greater challenge is teaching authors to use Word properly. (Why can't MS better document styles, templates, et al?) The time investment is definitely worth it for people who use Word on a regular basis.

BTW, when you convert Word to PDF in Acrobat, you can embed Word style information in the PDF in the form of tags, Adobe's answer to PDF accessibility issues. It works pretty well (if the Word doc has meaningful styles) and helps ensure your PDF files are 508-compliant.

Good luck.