Fair use is a mixed question of law and fact, and the fact issues will go to a jury (and in some cases, the judge will send it all to the jury). Without an actual trial, it's really hard to say what is fair use, unless what you are doing is something identical to say, an existing supreme court ruling :)
Granted, I did really, really like how GoldiBlox had to wear a proverbial dunce cap by putting a statement on their website to the effect of "We were wrong, way wrong, shouldn't have done that, and don't make the same mistake we did." Pretty epic. Also, it does go to show that hiring a law firm to tell you what you want to hear is completely possible, though fiscally dangerous.
What you can do is ask a lawyer if your idea is obviously not fair use and you'll get a straight answer. But you're not going to find someone who is going to say to you "yes, this is fine" because the law covering fair use is so vague. Laywers need to protect themselves when giving legal advice.
I'd recommend reading up on fair use and using your own brain. Case law is especially useful, i.e. many fair use cases regarding software have been to the supreme court - if you find a ruling covering something similar to your project then that is a good sign - Wikipedia and Google News are your friends.
I wouldn't do this for myself and I am lawyer capable of doing this sort of work for someone else.
You bias your own research when you are too close to the matter.
If you want a good rule of thumb for commercial fair use: Don't use copyrighted material at all unless you are doing a clear parody.
From Wikipedia:
The Supreme Court of the United States described fair use as an affirmative defense in Campbell v. Acuff-Rose Music, Inc. This means that in litigation on copyright infringement, the defendant bears the burden of raising and proving that the use was fair and not an infringement.
In other words, fair use is not "an exception" to copyright violation, but a legal process you can try to perform when you've been sued for copyright violation and concede that you copied (&c.) someone's work. If you've wound up in court, or even gone back and forth on a cease and desist letter, you have already drowned in inconvenience, cost, and lawyer time. You might be "right," but you've still been screwed by the copyright holder, who may be on the war path to make a point with a legal budget greater than your net worth.Remember: lawyers are responsible for practical advice, not intellectual, political, or ideological purity. They will be very sensitive to attempts to treat them as "lawyer-approved" stamp dispensers, and will assume an appropriately skeptical defensive stance. You may think the "substance" of fair use is more important than practicality and procedure, but a good lawyer will anticipate present risks and won't bother reading up on case law on your dime when, as a practical matter, that research and those arguments will never help you. A lawyer that gives you the bad advice you need to feel vindicated now might face reputation damage and potential malpractice liability later when bills mount and you suddenly wonder why your lawyer wasn't watching out for you. Yes indeed, it can be a lot more fun to go it alone on Google, following only links and leads that seem reassuring, a dog-eared Lessig book beside you and a Doctorow talk in the background to keep you warm.
You probably saw this coming: I'm not your lawyer, and this isn't legal advice meant for you or anyone else. If you have a legal problem, find a trustworthy lawyer. They'll ask questions to understand the specifics of your situation, which will affect what advice they give in ways you might not expect.
There are two questions you have to ask. One goes to the attorney's opinion of actual legality/defensibility. The other goes to likelihood that it will attract legal action. It's a business calculus.