Pen names and permissions

Hbooks said:

Three questions...

If I decide to go the self-publishing route and use a pen name, do I need to set up some sort of... I don't even know what... personal company? trademark for the pen name? or to publish under? (sorry if this is a dumb question... this whole process is confusing.) Like on the cover it would say pen name, obviously. Inside with the copyright, if I don't want it to say real name, do I put pen name, or how does that work since can you copyright something if that isn't really "you"? That's why I'm wondering if you need something legal like a TM or a personal company. (I understand pen names are not particularly hard to crack... just would rather not flash real name out there unnecessarily, either.)

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No. A pen name is just a name you're putting down as the author. It shouldn't require an LLC or a trademark.

Hbooks said:

Question two... in terms of being able to use brand names and real places, am I understanding that it's okay as long as you don't disparage the thing? Like is it okay for a character to drink a Sprite or wear Docs?

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It's always ok to use brand names and real places. The purpose of trademarks is to prevent confusion in the marketplace and reassure consumers that the manufacturer is one they trust. Trademark owners don't have a leg to stand on "defending" their brand from disparagement in fiction. But if it helps you sleep better, you can always invent a brand name if the story requires you to trash something. Stephen King did this with "Captain Trip's" cereal in The Stand.

When using brands or places in fiction, the most important consideration is to stay true to the POV. People don't say "Sprite(r) lemon-lime flavored soft drink is a trademark of the Coca-Cola Company" in real life, and your characters shouldn't use it that way either. Just capitalize and treat it as a brand rather than generic (drank a Sprite, not drank a sprite).

However, if you're writing non-fiction, avoid disparagement.

I manage several trademarks worldwide as part of my day job. One of our products was shown failing, leading to disaster in a major motion picture starring Robert Redford. We didn't mind; it was fiction, after all.

Hbooks said:

Three... I would have someone else make the cover art as that is out of my skill set. If one of the books has a few emoticons texted in it (I assume those are copyrighted) do I need to get permission/put something in there to use those images.

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I don't know about this. If it requires permission, do ask. But an alternative would be text emoticons like this :-D Those are not copyrighted. Nor are the emoticons/images inherent in fonts, unless the font requires copyright permissions to use in which case you'd need that permission anyway.