Taking your specific need first, the Windows Trademark Guidelines describes how to correctly refer to Windows-brand products. The upshot is that you should identify the product correctly (use the correct name) and you don't need the trademark symbol if the word is capitalized and clearly distinguishable. It also mentions that you should include a trademark notice in the credits or as a footnote.
Naming the supported versions of Windows Server in the user manual is fair use. (Note that no mark needed in the previous sentence!) Adding trademark symbols is primarily for the benefit of the trademark owner to maintain the strength of their trademark, and to clearly separate the trademark from surrounding text.
Generally speaking, you are allowed to cite the name of software, but not to include that name prominently into one of your products or advertisements without written permission.
Other relevant material: The python trademarks page has a good summary of what is fair use and not, and discusses nominative use and unapproved use - although it's written specifically for Python, it seems to be generally applicable.
See also http://xml.coverpages.org/trademarks.html for why they don't use trademark and registered mark symbols on the coverpages site, and When can I use another [...] company's Trademark without consent? from the International Trademark Association.
And of course, this is not legal advice.