You can license the same image over and over again. My salmon photographs are a major part of my stock library. The bulk of the work was done between 1986 and 1996. The licensing fees from those photographs are probably 10 percent of my annual income. Some of my wedding photographs are in my stock agencies. With the Mariners Book contract I reserved the right to license the photographs to third parties. I gave them the right to use the photographs for anything they wanted, except magazine stories. Photographs from the Mariners book continue to sell through Corbis. One of a guy mowing the outfield is the most licensed image I have at Corbis.
When in doubt, try to keep your right to use and license the images.
You never know when your image might be valuable. I shot an environmental portrait of a guy in 1986. In 2008 that portrait was licensed to a client by one of my agencies for an amazing amount of money. It had never been published before. Anywhere.
On the other hand there are times you choose to shoot in a “work for hire” contract.
I did the Microsoft book under one. I charged more than normal and knew that the job would be a long one. So basically all I can use the photographs for is promotion.
When granting licenses for your work make sure you know the true value of the images you are licensing.

www.corbis.com
www.sethresnick.com
asmp.org

What is the difference between stock and assignment licensing: Stock you are only selling usage. Assignment you are selling custom photography done to your client’s specs. You license creation and usage by either including the usage in the creative fee or by having it listed as a line item on top of the creative fee.
What are some of the benefits of listing it separately? If your client doesn’t like the quote you can negotiate out some of the usages (not the usage fee however)
What are some of the benefits of including it in the creative fee? (simplifies it for the client)
Either way you always have a very specific license for the usage in your terms and on your invoice.

What are some of the things you need to know to come up with a usage agreement?

Territory
Language
Term of usage
Media in which it will be used
How big or important is it going to be played
How many times
Exclusive or non-exclusive
Credit
In case of an ad, how much does the ad space cost in the media

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