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!
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Nice Article! It is very important to work under guidelines if you don’t want to get sued and don’t want to pay the penalties. But more importantly it is better to give each user hassle free user experience over your website. Being ADA Compliant means your website works well for people with disabilities and they can easily access and navigate your website.
The ADA itself holds different organizations to more/less stringent standards based on a host of factors, government funding being a major one. Government agencies themselves are usually held to the most severe standards. That said, while ADA has adopted WCAG as the defacto standard, from what I’ve seen it appears they’re going with AA compliance as the most reliable one. That said, we’ve done work with some organizations who’ve chosen to comply with AAA in an effort to be as buttoned up as possible from an accessibility and experiential perspective. We’ve also worked with some who have tighter budgers and aim for level A compliance and have a more “react and repair” mindset when they discover anything in their site that is giving someone hardship from an accessibilirt standpoint.

One of the first major ADA lawsuits, Paralyzed Veterans of America v. Ellerbe Becket Architects and Engineers (PVA 1996) was focused on the wheelchair accessibility of a stadium project that was still in the design phase, MCI Center (now known as Capital One Arena) in Washington, D.C. Previous to this case, which was filed only five years after the ADA was passed, the DOJ was unable or unwilling to provide clarification on the distribution requirements for accessible wheelchair locations in large assembly spaces. While Section 4.33.3 of ADAAG makes reference to lines of sight, no specific reference is made to seeing over standing patrons. The MCI Center, designed by Ellerbe Becket Architects & Engineers, was designed with too few wheelchair and companion seats, and the ones that were included did not provide sight lines that would enable the wheelchair user to view the playing area while the spectators in front of them were standing. This case[69][70] and another related case[71] established precedent on seat distribution and sight lines issues for ADA enforcement that continues to present day.
Until the ADA is updated to address the special case of website accessibility, or the Department of Justice releases its website accessibility regulations, complying with WCAG 2.0 Level AA is the best way to ensure that people with disabilities have equal access to your website. The overview below is a great starting point about meeting the WCAG 2.0 Level AA recommendations.
The ADA has been criticized on the grounds that it decreases the employment rate for people with disabilities[48] and raises the cost of doing business for employers, in large part due to the additional legal risks, which employers avoid by quietly avoiding hiring people with disabilities. Some researchers believe that the law has been ineffectual.[49] Between 1991 (after the enactment of the ADA) and 1995, the employment rate of men with disabilities dropped by 7.8% regardless of age, educational level, or type of disability, with the most affected being young, less-educated and mentally disabled men.[50] Despite the many criticisms, a causal link between the ADA and declining disabled employment over much of the 1990s has not been definitively identified.[51]

Web designers often design in such a way that does not allow the user to adjust font size or color. While they may be protecting their brand, they are also inhibiting some users. Many visually impaired need to use high contrast color settings or very large fonts to read a website. Don't design your website in a way that makes it impossible for them to do this. 
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. 
For most people, the Americans with Disabilities Act (ADA) conjures up pictures of physical accommodations such as wheelchair ramps near building entrances, handicapped parking spaces, and the use of braille writing on signs and placards. These measures have been tremendously valuable in helping the 56.7 million Americans with a disability function and thrive within society.
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.

Recent years have seen an uptick in federal lawsuits filed against businesses and governments, alleging that their website violates the ADA by being insufficiently accessible to people with disabilities. In 2017, there were at least 814 such lawsuits against organizations in a variety of industries, from banks and credit unions to restaurants and e-commerce websites. The defendants include small businesses as well as major corporations such as Nike, Burger King, and the Hershey Company.

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