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As you indicated, making the copyright owners happy is key to their allowing you to do what you want to do. Ultimately, all they are worried about is their profit, and as long as they believe your existence will earn them more of it in the long run, they won't give you much grief.
Using the characters, settings, names, etc, of Star Trek is really a trademark issue, not a copyright issue. Ethically speaking, Paramount has knowingly allowed you to use its trademark material thus far, which is a tacit acceptance that what you are doing is not objectionable to them. (This would be taken into account in most legal proceedings.) Obviously, this can change at any time, if you begin to create something new that does object to them--content-wise, stories about Kirk as an Orion slave girl pimp, for example, or material-wise, physical content that others can redistribute and resell--but in most cases, the trademark owner would voice their objection of that particular type of content or material, not all of it, as long as they do not believe your actions have irrevocably damaged the value of the trademark.
I'd say, give it a try. If you've never regularly communicated with them in the past, I wouldn't bother now... but if you have some means of making a public statement about your intentions beforehand, something Paramount could easily find or access, that would probably be enough to satisfy all parties. Then just be prepared to respond to any concerns voiced by Paramount, if any come up.
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