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I'd like clarification on this as well. My working assumption is that as long as we aren't tripping over any copyright/trademark issues (ex: Product Identity), we should be good. So for example my current plan is to do a supplement for Swords & Wizardry, which has a standing third-party compatibility license to use their PI and trademark. I assume that's OK?

Should be, yes. If you're concerned about trademarks and copyrights, the thing to keep in mind most is is what you're making for commercial purchase or not. 

If no, and you're not using artwork or images that require a commercial license, you're fine. 

should be