What documents should I have on my website to make it so when people upload files they grant me a license to display them?

You need terms of service (a/k/a terms of use) and they need to have been agreed to by the person making the upload (not difficult, but assuming your business is in MD, you will want to comply with UCITA; if not, then you need a full click/web wrap - which many sites do anyway). But . . . there is more to consider. For example - you probably need to register at the Copyright office for notice and take down issues to avoid copyright liability, you need to know the rules on CDA immunity to...

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Can I paint an NFL logo on a friends private swimming pool for money? If not can I do it for free?

The NFL is a notoriously active trademark enforcer, and even if this is fair use, or even if the use is not a "trademark use" you are still going to have issues with the NFL - no one has mentioned Section 1125 of title 15, but that is the area where you may have an issue - because by doing this for him, it may appear that you are affiliated with or authorized by the NFL to perform such services. Sometimes a disclaimer works; but I have dealt with the NFL before, as well as Ford, and Honda, in...

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I wish to use a Hello Kitty image on a spare tire cover (not the Hello Kitty name) Is that considered Trademark Infringement?

It is not clear what you are doing - if you are going to apply the "Hello Kitty" image to any product and sell the product, as others point out, you would need a license from the trademark owner (trademarks apply to images as well as names, if the image is used as a trademark, and that one clearly is). If, however, you purchased something already with the Hello Kitty on it (like a shirt or towel or something) and you are just going to cut that out and attach it somehow to a tire cover for...

Follow-up: Can I use a blank outline map (borders only) made using a copyrighted map in a product that I plan to SELL?

Your best bet is to use maps created by the US Government. In general the US government cannot copyright its own works (be careful though, the US government can purchase copyrighted works of others and retain copyright). Do a search in Google and limit the search to .gov sites, and explore. Then just check the footer and make sure the maps are free. Most are. You can also purchase royalty free images for pretty cheap at many sites, just google royalty free map. To perhaps answer a bit...

Can I sell fashion illustrations of designs from the runway?

The prior respondent seems to suggest that you always must get permission, and I disagree with that. From Nimmer: "Statutory copyright protection is largely unavailing for dress designs ... a clothing garment constitutes a ''useful article'' within the statutory definition, ... [while] a fabric design is capable of such separate identification and independent existence [] a dress design typically is not." Having said that, you would need to consult with a lawyer if you really intended on...

What kind of trademark do I need?

Before you jump to filing a trademark, ask yourself what are you trying to protect and how much money and advertising and effort are you going to expend? Federal trademark registration requires use "in commerce" meaning, typically, use among the states and not solely affecting a single state's commerce. If you want to create a nationwide car club (or even a regional one around MD, PA and WV) and license the right for local chapters, you need to speak to a lawyer, because that may involve not...

How different is different enough?

You have to change it more substantively than slightly modifying the prefix of the mark. "Beast" "Beastly" "Beasty" will be effectively equivalent in trademark law. However, changing the word to something not phonetically equivalent but possibly synonymous could work (assuming that the new mark is not likely to be confused with another holder). For example "Monster Bat" or "Ogre Bat" or something like that. Sometimes adding a source identifying and material graphic stylization can help, or...