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I do not know of any sites other than the main job sites, i.e. Monster, HotJobs, CareerBuilder, and one I seldom use, Dice. The "Career" section on iWon.com lists jobs that are sometimes not listed on the mainstream sites. In addition, I would check the online employment section of your local newspaper, or the newspaper(s) in the city you are interested in.
Also be sure to check your state's Job Service website. I recently lived in Minnesota and there were numerous tech writing jobs listed on the state site that were not listed anywhere else. I would like to point out that the jobs were with companies and were not government jobs. Another site that I have used is America's Job Bank. Again, lists many positions not found anywhere else.
However, I am unsure how many of these will prove useful to you as you are looking for a telecommuting position. I do not know enough about the "nationwide" positions that are commonly listed on the websites such as Monster, HotJobs, and CareerBuilder to make any kind of justified statement. And it has been a few months since I accessed AJB, or a Job Service page, and I am not sure if you have or not, and if not, it might be a direction you can take.
Lastly, I did visit a few tech writing job sites a few months ago that were for contract writers. It was set up like an auction site where you bid on jobs, and many of them were telecommuting in nature, BUT I must state that I did NOT investigate any further as at the time I was searching for full-time employment.
I hope this info is beneficial. As for your other inquiry, I do not know of any websites with used documentation software.
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