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If you are going to use the attributed quote of a living person on a product, I think in most cases you would have to get their permission and perhaps negotiate a royalty.
Using a computer font to create a for profit item (say, the lettering on a coffee mug) almost certainly falls within the license. Reselling the font itself in some manner is probably a violation.
On all intellectual property issues, it's better to get the advice of an attorney. Business opinions from forum posters can point you in the right direction, but shouldn't be relied on for legal decisions.
2. Depends on the font. Some are copyrighted. If you have purchased the right to use a font, then you can generally use it in any context. See point #3
3. For both your questions, it's difficult to answer without knowing much more, and you should not rely on the off-the-cuff opinions expressed here. Get a lawyer with experience in copyright issues, and have him or her review what you want to do. Cheaper in the long run than being sued.
[added] Looks like you've been double-teamed....
You need to check the license agreement for each font you want to use for such a purpose.
In most cases, if you legally purchased the font, you're going to be okay if you use the font to create a newsletter for sale, your packaging materials for your item, etc. But, again, check the license agreement.
Be aware that if you distribute something like a newsletter as a PDF, some companies restrict you from embedding their font in the file.
Where you'll probably run into more restrictions is if you want to use the font to create some type of artwork derived from that font, such as a t-shirt whose only artwork is typing a word or phrase in that font. Such items may include t-shirts, caps, mousepads, rubber stamps, clip art, buttons, etc. Some companies may require a higher license fee or royalties for such purposes. Check the license agreement, and inquire directly with the font manufacturer if you have any questions regarding the agreement.