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I have seen no evidence that Amazon pays any attention to content loaded from other sites. There are some people who are suspicious that Amazon monitors the content on their Kindles. I've never worried about it. I buy a lot of DRM-free books from other retailers and don't think another thing about it.
Certainly it is possible for Amazon to obtain a list of the files on your Kindle -- that's how they keep up with the current location of your purchased content in the Content Manager application. But would Amazon pay any attention to books whose titles are NOT in the format that they use? I'd think it would be too much trouble.
If, however, your current best sellers are coming from dubious providers (i.e. the dark net) you might want to keep the antenna turned off while this content is on your reader -- just in case. My only concern would be if a court subpoenaed your Kindle info from Amazon to investigate for possible copyright infringements. Seems to me that the court could catch you obtaining infringing content much easier by just tapping your Internet connection or confiscating your PCs.
(How's that for conspiracy theories?)
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