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.

The Americans with Disabilities Act was instituted in 1990 in an effort to end discrimination based on differing abilities. Drawing heavily from the landmark Civil Rights Act of 1964, which established protections against discrimination based on race, religion, sex or national origin, the ADA went a step further by requiring organizations to provide “reasonable accommodations” to employees with disabilities.
According to Creating an Accessible Presence for the Lodging Industry by the American Hotel & Lodging Association, “Many businesses don’t understand that the law actually requires them to make their websites accessible to individuals with disabilities. There is a common misperception that the Americans with Disabilities Act and similar state and local laws only deal with physical buildings and facilities, so-called “brick and mortar” establishments, and that non-building-related business operations—such as websites—are not covered by these laws. Nothing could be further from the truth—at least with respect to websites that have some sort of connection, or “nexus,” to physical places of business.”

Aside from attempting to compliant for compliance’s sake, having an ADA accessible website can improve the overall user experience and site traffic. An ADA compliant site can increase your target audience (by making it easy for those with disabilities to navigate around), improve your SEO efforts (by helping search engines to more easily crawl your pages and content), and help your overall reputation.
Thanks for writing. While I’m not a lawyer I believe if your physical practice is ADA exempt your web presence, as an extension of that physical business would maintain the same exemption status. If you’d like to be absolutely certain I’d confer with an ADA lawyer (email us, questions at yokoco dot com if you need a referral) but I don’t believe you have reason to worry.

The fastest, most certain way to be sure your website is in compliance is to contact a qualified web design agency and have them perform an audit of all your online properties. Make sure you interview the agency thoroughly first, as not all agencies are up to speed on ADA website compliance rules. A qualified web design firm will be able to identify any violations of ADA Website Compliance and outline a plan for updating your online content and properties. 
“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.)
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.
Because they only read text, screen readers and refreshable Braille displays cannot interpret photographs, charts, color-coded information, or other graphic elements on a webpage. For this reason, a photograph of a mayor on a city’s website is inaccessible to people who use these assistive technologies, and a blind person visiting the website would be unable to tell if the image is a photo, a logo, a map, a chart, artwork, a link to another page, or even a blank page.
Hey Casey, this is one of the areas where things get a little weird because the W3 doesn’t actually have any say over the ADA guidelines, it is more than the ADA guidelines adopted the WCAG 2.0 guidelines as just that, a guideline to help. As far as I know, the tool you’ve linked to hasn’t been used in any judgements I’m aware of. Usually when it comes down to making a decision on if something is/isn’t compliant they have people use the actual PAWS tools and show what elements do/don’t work as intended or are otherwise inaccessible. Hope this helps!
“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.)
Technology is changing, and many website designers are using creative and innovative ways to present web-based materials. These changes may involve new and different access problems and solutions for people with disabilities. This Chapter discusses just a few of the most common ways in which websites can pose barriers to access for people with disabilities. By using the resources listed at the end of this Chapter, you can learn to identify and address other barriers.
Another important consideration is that the ADA does not allow businesses to simply provide an alternative such as a phone number. Lastly, include accessibility issues as part of your website and mobile strategy. When new technologies are implemented or pages added, part of the process should include the implications for persons with disabilities. 
Poorly designed websites can create unnecessary barriers for people with disabilities, just as poorly designed buildings prevent some people with disabilities from entering. Access problems often occur because website designers mistakenly assume that everyone sees and accesses a webpage in the same way. This mistaken assumption can frustrate assistive technologies and their users. Accessible website design recognizes these differences and does not require people to see, hear, or use a standard mouse in order to access the information and services provided.
Most recently, however, pizza chain Domino's has been brought under suit for their website not being accessible for specialty ordering. The U.S. Supreme Court refused to review the case, instead upholding the decision of the 9th U.S. Circuit Court of Appeals who said the “alleged inaccessibility of Domino’s website and app impedes access to the goods and services of its physical pizza franchises—which are places of public accommodation.”
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