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What do you want your website to look like? Consider websites that are similar to the one you’d like to build, ideally in the same industry or serving similar types of customers. Build a set of examples of types of pages, design aspects, and website features that you can hand off to the web designer — the person you hire should have experience creating websites with the features you want. If they don’t have the right skill set, they’re not the right pro for you.
The legal issue for websites is whether website operators are operating “a place of public accommodation.” The statute lists 12 different types of public accommodations including somewhat of a catchall that includes “other sales or rental establishment.” The list, created when the law was passed in 1988, conceivably covers most commercial establishments, but does not expressly include websites.
The question of ADA’s exact wording comes down to two issues: 1) whether the ADA applies to a website at all, and 2) if ADA applies only to websites that have a physical connection to goods and services available at a physical store or location, or if it applies to all websites even if they don’t have physical spaces. Courts are split on these issues but one thing is for certain: the tide is moving toward ADA compliance for websites, and the lack of specific legal wording prohibiting web discrimination has not stopped businesses from being sued.
Level AA is a little more significant, and makes sites accessible to people with a wider range of disabilities, including the most common barriers to use. It won't impact the look and feel of the site as much as Level AAA compliance, though it does include guidance on color contrast and error identification. Most businesses should be aiming for Level AA conformity, and it appears to reflect the level of accessibility the DOJ expects. 
UPDATE: Since writing this post in August 2017, several important changes have taken place in the laws regarding ADA compliance for websites. On December 26, 2017, the Department of Justice announced that they have withdrawn the Obama-era Advance Notice of Proposed Rulemaking mentioned in this article which intended to require ADA website compliance. The DOJ’s withdrawal announcement stated, “The Department will continue to assess whether specific technical standards are necessary and appropriate to assist covered entities with complying with the ADA.”
“Any business that is considered a “place of public accommodation” is required to provide equal access to services under the nondiscrimination requirements of Title III of ADA. When you look at the guidelines closely, this includes hotels, entertainment venues, legal and accounting firms, retail stores, and virtually every business that is not a private club, including businesses that exist solely on the web.” (Read full article.)

This past September marked the first time a judge ruled that the ADA applies even to businesses without a physical location. Scribd, an e-book subscription service is considered to provide "a place of public accommodation." Their services are not accessible to blind persons because they cannot be read with a screen reader. The judge reasoned, "Now that the Internet plays such a critical role in the personal and professional lives of Americans, excluding disabled persons from access to covered entities that use it as their principal means of reaching the public would defeat the purpose of this important civil rights legislation."
The ADA statute identifies who is a person with a disability, who has obligations under the ADA, general non-discrimination requirements and other basic obligations. It delegates fleshing out those obligations to federal agencies. The agencies issue regulations and design standards. The regulations have the details on the rights of people with disabilities and responsibilities of employers, state and local governments, transportation providers, businesses and non-profit organizations. The design standards specify how many entrances need to be accessible, how many toilet rooms and the design for those elements.  To know what the ADA requires, you need to read the law, regulations and design standards.  
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