The gray area is a matter of scale and purpose. If you have a small business which serves as specific market it's a good idea to make the site as user and disability friendly as possible. If, however, your market serves segments with a likeliness to have various handicaps or disabilities you should address that with an ADA Compliance review of the site. Also consider the scale and purpose of an organization. Publicly traded large businesses need to concern themselves more than a single location family owned retailer and if someone sues your flower shop because the text was too small or didn't have "image alt tags" causing them distress... That's pretty frivolous and would likely not stand.
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 On December 26, 2017, the Department of Justice announced that they have withdrawn the Obama-era Advance Notice of Proposed Rulemaking mentioned in this article which intended to require ADA website compliance.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.”
That carousel or image slider on your site looks beautiful. That stunning video on autoplay may have cost thousands to produce. Users with cognitive limitations, however, may not comprehend your information quickly enough before the view changes or your video ends. Other users may want to start over, or go back and review something they saw or heard.
Another federal agency, the Architectural and Transportation Barriers Compliance Board (ATBCB), also known as the Access Board, issues guidelines to ensure that buildings, facilities and transit vehicles are accessible to people with disabilities. The Guidelines & Standards issued under the ADA and other laws establish design requirements for the construction and alteration of facilities. These standards apply to places of public accommodation, commercial facilities, and state and local government facilities.
Two agencies within the U.S. Department of Labor enforce parts of the ADA. The Office of Federal Contract Compliance Programs (OFCCP) has coordinating authority under the employment-related provisions of the ADA. The Civil Rights Center (CRC) is responsible for enforcing Title II of the ADA as it applies to the labor- and workforce-related practices of state and local governments and other public entities. Visit the Laws & Regulations subtopic for specific information on these provisions.
The words in the tag should be more than a description. They should provide a text equivalent of the image. In other words, the tag should include the same meaningful information that other users obtain by looking at the image. In the example of the mayor’s picture, adding an “alt” tag with the words “Photograph of Mayor Jane Smith” provides a meaningful description.

The fact that an ADA compliant website can increase your target audience by millions is just one reason to make your site more accessible. Another benefit is that not only will you get more customers, but those customers will also know how valuable they are to your business. After all, they might have gone to a few other websites that were not ADA compliant, disappointed each time that they couldn’t access the content, until they got to your website.

These rules nearly made their way to the Supreme Court in 2019. In 2016 a web accessibility civil suit was filed against Dominos Pizza. In the following years, the case filtered through layers of judgements and appeals, and Dominos eventually appealed to the Supreme Court. Unfortunately, the Supreme Court declined the case and returned it to a lower court. Though this provides no final clarification, the ruling by a lower court in favor of the plaintiff supports the legal requirements for web accessibility.
While legal considerations might be your biggest worry, making your site more accessible is simply good customer service. More than 39 million Americans are blind and another 246 million have "low vision," Another one million are deaf in the U.S. Add to that people with mobility issues that prevent them from using their hands and that's a huge portion of the country's buying power.
Case law has been the most helpful in illuminating the implications of the ADA for websites.There have been lawsuits involving companies like Expedia, Hotels.com, Southwest Airlines, and Target as defendants and primarily featuring accessibility organizations as plaintiffs. These cases had mixed results, but each helped clarify the ADA's jurisdiction on the web. 

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If posted on an accessible website, tax forms need to be available to people with disabilities in an accessible format on the same terms that they are available to other members of the public – 24 hours a day, seven days a week, without cost, inconvenience, or delay. A staffed telephone line that sent copies of tax forms to callers through the mail would not provide equal access to people with disabilities because of the delay involved in mailing the forms.

HTML tags – specific instructions understood by a web browser or screen reader. One type of HTML tag, called an “alt” tag (short for “alternative text”), is used to provide brief text descriptions of images that screen readers can understand and speak. Another type of HTML tag, called a “longdesc” tag (short for “long description”), is used to provide long text descriptions that can be spoken by screen readers.

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