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.
For close to seven years, since July of 2010, the United States Department of Justice (DOJ) has talked about issuing regulations specifically about web accessibility. At that time the US Department of Justice (DOJ) began developing accessibility guidelines for public websites under Title III of the Americans with Disabilities Act (ADA). On December 26, 2017, the Department announced that those regulations were officially withdrawn.

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The Americans with Disabilities Act (ADA) and, if the government entities receive federal funding, the Rehabilitation Act of 1973 generally require that state and local governments provide qualified individuals with disabilities equal access to their programs, services, or activities unless doing so would fundamentally alter the nature of their programs, services, or activities or would impose an undue burden.2 One way to help meet these requirements is to ensure that government websites have accessible features for people with disabilities, using the simple steps described in this document. An agency with an inaccessible website may also meet its legal obligations by providing an alternative accessible way for citizens to use the programs or services, such as a staffed telephone information line. These alternatives, however, are unlikely to provide an equal degree of access in terms of hours of operation and the range of options and programs available.
The ADA is a civil rights law that prohibits discrimination against individuals with disabilities in all areas of public life, including jobs, schools, transportation, and all public and private places that are open to the general public. The purpose of the law is to make sure that people with disabilities have the same rights and opportunities as everyone else. The ADA gives civil rights protections to individuals with disabilities similar to those provided to individuals on the basis of race, color, sex, national origin, age, and religion. It guarantees equal opportunity for individuals with disabilities in public accommodations, employment, transportation, state and local government services, and telecommunications.
The 2014 case involving Peapod, an online grocery retailer emphasizes that being ADA compliant goes beyond your website. The settlement required Peapod to make its mobile applications accessible by March 2015 and its website accessible by September 2015. Since mobile apps are fast becoming the preferred method of online shopping, e-commerce sites must focus on app accessibility too. 
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!
Conclusion: This article covers only the basics behind ADA accessible websites. You can find further detailed information at www.ada.gov. Since most current websites are not yet fully ADA accessible, it is important for you to begin the process now. But be forewarned. The consequences of not becoming ADA accessible can be expensive. The potential of penalty fees, lawsuits, and lost business are all powerful reasons to be ahead of the curve when it comes to ADA accessibility for your website. To make sure your website meets the necessary ADA guidelines, select a website design and consulting firm that specializes in ADA accessible websites and online reservation systems. As always, RezStream is happy to assist lodging properties of all sizes in ADA consulting and website design services. Please call RezStream toll-free at 866-360-8210 for more information on this timely topic.
There are several phases to go through to make a website ADA accessible. First, it is important to have your existing website evaluated for ADA accessibility. Have this evaluation done by a company that specializes in ADA compliance for lodging properties. Most existing websites will not pass a detailed ADA evaluation. Depending on the results of your professional ADA inspection, you will either have to make necessary changes to your existing website, or have it redesigned to meet ADA accessibility guidelines. 
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.
As organizations around the world scramble to bring their sites into compliance with the World Wide Web Consortium’s Web Content Accessibility Guidelines (WCAG), focus on other, preexisting accessibility regulations has also intensified. The United States’ Americans with Disabilities Act (ADA) is one of the most visible and complicated pieces of accessibility legislation. Let’s look at some of the ins and outs of what an ADA compliant website means today. Or, if you're interested in seeing the nitty-gritty details of your site's accessibility, request a free website audit report using the form on this page.
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