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.
Since March 15, 2012, ADA compliance with the 2010 Standards will be required for new construction and alterations. In the period between September 15, 2010 and March 15, 2012, covered entities may choose between the 1991 Standards ADA Compliance (without the elevator exemption for Title II facilities), the Uniform Federal Accessibility Standards (Title II facilities only), and the 2010 Standards ADA Compliance.
The legal issue for websites is whether website operators are operating “a place of public accommodation.” The statute lists 12 different types of public accommodations including somewhat of a catchall that includes “other sales or rental establishment.” The list, created when the law was passed in 1988, conceivably covers most commercial establishments, but does not expressly include websites.
Because web designers tend to work as freelancers on a project basis, they must be excellent communicators, willing to manage their own work, and available on your schedule. Some critical skills, such as working collaboratively and responding enthusiastically to feedback, aren’t core to good web design, but make working with a web designer much easier. Finally, look for a web designer who has cross-functional knowledge, such as understanding marketing and conversion rate optimization in addition to web design.
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.
Yes, as of 2018 websites absolutely must be ADA compliant.  Its a new but very scary issue that has flared up over the last year and is set to cause a LOT of turmoil.  The Supreme court issued a judgement that opened up a loophole and opportunity-chasing lawyers are aggressively soliciting handicapped people and convincing them to sue unsuspecting website owners (pretty much every website owner on the planet, as not a single one of us were ADA compliant before now.)
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.
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.

I am struggling with this right now. Alt text, captions, audio (read to me) options are good. I work with an accounting software app that redesigned its palette to red, black, and gray. No green to signify income. Made no sense to me and their gray text (also very skinny sans serif) made reading many nav bars difficult. Some URLs are accessible from the build-out, but the DIY sites often don't have the same capacity. As with secure sites, I think google will be downgrading those sites with little or no compliance or accessibility add-ons.
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No online tool can cover all the issues of ADA accessibility. To make sure your website meets the necessary ADA guidelines, employ an ADA compliance specialist that will review your website. Specialists are much better at evaluating the consistency of your website content as well as your current online reservation system. Furthermore, you will get the best results by combining the test results of online tools with the experience of an ADA compliance specialist.
Your website is often the first thing your customers see when they’re searching for a business or service on the web. As the face of your organization, your website needs to be attractive and functional, offering the latest features that users now expect. To plan and design a site that both reflects your company’s mission and values and appeals to customers takes a professional web designer. While free online services can help people set up websites, web designers can provide a unique solution made specifically to meet customers’ personal or business needs.
The ADA statute identifies who is a person with a disability, who has obligations under the ADA, general non-discrimination requirements and other basic obligations. It delegates fleshing out those obligations to federal agencies. The agencies issue regulations and design standards. The regulations have the details on the rights of people with disabilities and responsibilities of employers, state and local governments, transportation providers, businesses and non-profit organizations. The design standards specify how many entrances need to be accessible, how many toilet rooms and the design for those elements.  To know what the ADA requires, you need to read the law, regulations and design standards.  
People with disabilities are all around us. They live in every country and often experience life in a very different manner than those individuals who don’t have emotional, mental, or physical disabilities. In fact, 15 percent of the global population is classified as disabled. Of this 15 percent, an estimated 190 million people experience significant disabilities.¹

The ADA guidelines provide the foundation that organizations need to achieve digital accessibility best approaches, however they are not exhaustive. They do not provide direction for all of the accessibility challenges that people with disabilities face. They also fail to provide detailed technical instructions. With these limitations in mind, there is a ray of hope.
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.
Courts have essentially taken three positions when approached with this issue. Some courts take the position that the ADA applies to all commercial sites because the law was meant to protect disabled individuals from having a more difficult time than able-bodied individuals from doing business. That is why the website Scribd was unable to get a case summarily dismissed and ended up settling.

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.
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