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.
"Candyce's company has done work for me for close to 5 years and has done a superb job with everything from business card design, to marketing materials like case studies, sales proposals, PDF brochures, as well as updating our Website. Her designs are always fresh and new so it is not the same recasting of old designs. Very reliable, also at times when we have to complete...
In short, the ADA is meant to protect disabled individuals as they go about their daily lives. These regulations ensure that people with disabilities are not denied entry into the above places or denied services by a company due to their disability. It is important to note that these regulations are now applicable to services that are provided online or through other digital formats. For example, if a company accepts job applications online, then it must ensure that a person with a disability can also apply for the job online. In other words, it is illegal to have barriers on the website that would keep the disabled individual from successfully completing their application. Fortunately, the ADA guidelines help to remove barriers and ensure that the Internet remains a space that people of all backgrounds and disabilities can use.
The way a lot of people think about getting a new website is, they have a certain amount of money and they think, If I pay less money for a website, I'll have extra money left over, therefore I win. And so they'll go and get a Square Space or a Wix or a Go Daddy website, and they'll think because they've saved money they're coming out ahead of the deal.
In short, the ADA is meant to protect disabled individuals as they go about their daily lives. These regulations ensure that people with disabilities are not denied entry into the above places or denied services by a company due to their disability. It is important to note that these regulations are now applicable to services that are provided online or through other digital formats. For example, if a company accepts job applications online, then it must ensure that a person with a disability can also apply for the job online. In other words, it is illegal to have barriers on the website that would keep the disabled individual from successfully completing their application. Fortunately, the ADA guidelines help to remove barriers and ensure that the Internet remains a space that people of all backgrounds and disabilities can use.
While some might be tempted to do this if you understand anything about how Google indexes websites, someone who has thousands of pages on their site would lose rankings. The price of making your site fully accessible depends on how large your website is. Making the best decision for your specific situation is best done by consulting a professional.
In a society in which business is increasingly conducted online, excluding businesses that sell services through the Internet from the ADA would ‘run afoul of the purposes of the ADA’” in that it would prevent “‘individuals with disabilities [from] fully enjoy[ing] the goods, services, privileges, and advantages, available indiscriminately to other members of the general public.
Title III of the Americans with Disabilities Act (ADA) prohibits discrimination on the basis of disability in places of public accommodation, including restaurants, movie theaters, schools, day care and recreational facilities, and doctors’ offices. All public places, as well as privately owned commercial facilities, are required to comply with ADA standards.

This is the reason why I think web design firms have to position themselves as solution providers and not just web guys/gals. A client doesn't need a website, they need sales. The website is just part of that solution but it's not the solution and unlike web design, service like email marketing automation, SEO, and PPC requires an experienced professional.
Upon discovering issues faced by disabled government employees and the public, revisions to section 508 were made. The issues that were uncovered involved websites, documents, and software programs. As of January 2018, the updated 508 standards require all federal agencies and contractors to create web content accessible to all. The updated standards also include Website 508 compliance.
As I mentioned above, under each WCAG 2.1 principle is a list of guidelines, and under each guideline are compliance standards, with techniques and failure examples at each level. Some guidelines include only Level A items; others include items for multiple levels of conformance, building from A to AAA. At each stage, you can easily see what more you would need to do to reach Level AA or AAA. In this way, many websites include elements at multiple levels of accessibility.
What’s the scope of the work? Will the website be basic with just a few pages about your company, its services, and contact information? Or will it also have an e-commerce section for online shopping, a blog, or content for visitors to download? Before you hire a web designer, make sure you have a thorough, specific list of the components you must have the designer include in the web design.
WCAG guidelines break accessibility issues down into three levels. Level A issues are the most urgent and include problems that can severely limit a disabled visitor’s ability to navigate or use the website. Level AA issues tend to be more rooted in functionality, addressing areas where improvement is needed to give disabled users the full experience of a site. (Level AA is considered the target standard for most commercial websites.) Level AAA issues are the highest standard, fine-tuning and expanding on issues identified as Level A and AA. While it is an excellent goal, full Level AAA compliance is likely beyond the reach of most websites.
The need to make websites, mobile apps, and other online properties accessible to all is only going to increase as time moves on. Smart business owners will do well to get in front of this issue and make sure that their websites are ADA compliant now so that all their customers have the equal access to the resources they offer. Not just because they want to avoid a lawsuit or government action, but because it’s the right thing to do.
The U.S. Department of Transportation enforces regulations governing transit, which includes ensuring that recipients of federal aid and state and local entities responsible for roadways and pedestrian facilities do not discriminate on the basis of disability in highway transportation programs or activities. The department also issues guidance to transit agencies on how to comply with the ADA to ensure that public transit vehicles and facilities are accessible.
...the full and equal enjoyment of the goods, services, facilities, or accommodations of any place of "public accommodation" by any person who owns, leases, or operates a place of public accommodation. Public accommodations include most places of lodging (such as inns and hotels), recreation, transportation, education, and dining, along with stores, care providers, and places of public displays.

The DOJ is currently working to release new technical standards for digital accessibility. The latter updates to the ADA guidelines will be in conjunction with the latest version of WCAG 2.1, which includes the most widely accepted digital accessibility requirements across the globe. If organizations want to overcome the current limitations of ADA guidelines, then they should follow the WCAG 2.1 checklist,11 as well as the suggestions provided by the ADA. The latter two steps, combined with the help of a trusted digital accessibility compliance platform,12 can help organizations achieve digital accessibility best in class standards throughout all of their digital formats and across all media.
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. 
Creating a more operable and navigable website will ultimately benefit all users while still meeting WCAG guidelines. Making your web pages easier to comprehend will allow everyone - disabled or non - to find what they’re looking for quickly. If you decide to follow the guidelines, your website will likely convert more leads across the board because users will trust that they can always easily find the content they need.
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.
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