Tunalover,
I am running Linux at home. I write a lot of documents with LaTeX. I use Xfig to draw vector graphics. I use a Makefile to generate the document in PDF and/or HTML format. From LaTeX, I can generate online documents with linked tables of contents. One of the nice things about Xfig is that there are command line tools for extracting EPS or PDF copies of its files. I can write a command line script, like a Makefile, that builds the final document out of the latest available files. LaTeX is available for Windows. There is something out there called WinFIG. Transfig provides the command stuff that extracts the FIG files.
For the purposes of CAD drawing, Xfig is not as good as a decent CAD package. It does not do intelligent dimensioning.
Your next choice is to generate your drawings in some available CAD package, and save them in EPS format. You will have to update your graphics and the EPS copies, manually. Your graphics would have to be imported manually into your Microsoft Word or Open/Libre Office files. If you use the word process styles properly, you can add a table of contents.
I write stuff in straight HTML, using a text editor. Xfig is exportable to PNG, JPEG and GIF format. It does anti-aliasing, so your graphics will look as good as you can make them in Xfig. Once again, you have the ability to use a script, like Makefile or Microsoft BAT, to generate the latest version of your web page.
Another useful Linux utility is Image Magick. This appears to be available for Windows. It was the big Linux graphics program before the GIMP came along. It still provides command line utilities that will copy and resize your photos, change the quality, and add copyright notes. This is very useful again if you use any sort of build script for LaTeX or HTML.
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JHG