Edwin,
I'm not sure I understand your question. With whom are you worried about "getting in trouble?" In the search engines, no one. Remember, the so-called "duplicate content penalty" has to do with which content is displayed first in search results. For all the talk about Google penalizing people for duplicate content, they certainly display many versions of the same "stuff" in search results.
When you submit original articles to article directories, you still hold the copyright. You are merely syndicating your work, allowing others to publish it, but without their taking credit for your articles.
Some directories, however, want unique articles that no one else has published, including on your own site. In that case, depending on the directory, you are, in a way, licensing your work to them, and they pay you when someone pays them to use your work.
If you take that content and re-use it without modifying it substantially, then you are probably in violation of the rules you agreed to with that directory.
BUT, if you have no such agreement with a paid directory, and instead you submit your work to, say, Ezinearticles.com, it is still your article. You can take that content and do pretty much whatever you want.
THAT SAID, I would recommend, however, that you modify anything you've submitted to the directories before you use it, because it will take very little work and you will then have similar but different content. In my opinion, this is to your advantage.
I would never recommend taking something you've created in the past and now have syndicated, and then cutting it up into an autoresponder series or turning it, "as is" into a PDF and calling it an ebook. Here's why I say that -- and remember this is my opinion:
Let's say a customer, we'll call her Jane Doe, reads your article on someone's website. Then a few months later she sees an ebook for sale on the same topic and she buys it. When she opens it up and finds it word-for-word the same as an article she read, don't you think she would be upset? I know that I would be furious that I'd just paid for something I could get for free elsewhere, and in fact, had already read it for free.
Repurposing takes a little work. Here's what Jeff Herring, "The Article Guy," recommends doing with articles. He likes the "tips" format. So you write one article giving 7 tips, in about 500-700 words. Then you take each tip and write an article about it, giving you 8 articles in all. My recommendation would be to submit the 7 tips (or 5 or 10 or whatever number) article to directories and then use the expanded articles on each tip for your other content.
Does this answer your question?
Deb Gallardo