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.
You are correct, ADA defines an “employer” as any person who is 1) engaged in an industry affecting commerce; 2) employes 15 or more full-time employees each work day; and 3) for at least 20 or more calendar weeks in the year. In the context of physical spaces, ADA would not apply to companies with fewer than 15 employees. However, courts don’t seem to have come to a consensus on what digital compliance really should look like. Because websites can be accessed anywhere in the country, small business owners might potentially face lawsuits in unfavorable jurisdictions. If you are a small business owner, I would recommend consulting with an accessibility lawyer and ask what they recommend.
The ADA’s relationship with websites has been a complicated and often confusing story. The ADA does not explicitly address online compliance, even after undergoing several amendments in the far more web-oriented era of 2008. With no specific coverage under the law, it usually falls to the courts to determine how ADA standards apply to websites—or whether they do at all. 
These rules nearly made their way to the Supreme Court in 2019. In 2016 a web accessibility civil suit was filed against Dominos Pizza. In the following years, the case filtered through layers of judgements and appeals, and Dominos eventually appealed to the Supreme Court. Unfortunately, the Supreme Court declined the case and returned it to a lower court. Though this provides no final clarification, the ruling by a lower court in favor of the plaintiff supports the legal requirements for web accessibility.
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.
Now you know that some types of content and format on webpages can pose barriers for people with disabilities. The next steps are to develop an action plan to fix web content that is currently inaccessible and implement procedures to ensure that all new and modified web content is accessible. The website accessibility checklist included in this section helps you assess what needs to be done.
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.
Most web designers offer a wide variety of services to make your website aesthetically pleasing and easy to use. Modern web design must be mobile-friendly and scalable, capable of expanding to include a blog, social media sites, and even video streaming; web designers are experts at integrating various web technologies. They can build the site, add functionality, test it, launch it on a live server, and track and maintain its performance.
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.

The truth is, when you’re assembling like a furniture, you’re not a professional furniture builder, and therefore the quality and the output is not going to be as good. And that metaphor applies to website design. Most people are not professional digital marketers or designers or understand user personas, or how to get traffic, or any of those things. And so, not only are you using all of your time to build the website but then you’re not getting as high-quality an output as you would as if you just hired someone who did that full time.
Yes, all websites must have hand rails in the rest rooms, ramps in lieu of front porch stairs and elevators with doors wide enough for wheelchairs to be easily loaded into them. Seriously though, ADA only covers Americans, and the Internet is hardly just an American institution. Besides, browsers can already be configured to override the web designer’s pre-configured fonts, font sizes, font and page and page background colors, etc, to make it much easier to read. Also, the big 3 Operating Systems (MS Windows, MAC, and Linux) have text-to-speech programs which will allow the computer to read... 

Videos need to incorporate features that make them accessible to everyone. Provide audio descriptions of images (including changes in setting, gestures, and other details) to make videos accessible to people who are blind or have low vision. Provide text captions synchronized with the video images to make videos and audio tracks accessible to people who are deaf or hard of hearing.


The truth is, when you’re assembling like a furniture, you’re not a professional furniture builder, and therefore the quality and the output is not going to be as good. And that metaphor applies to website design. Most people are not professional digital marketers or designers or understand user personas, or how to get traffic, or any of those things. And so, not only are you using all of your time to build the website but then you’re not getting as high-quality an output as you would as if you just hired someone who did that full time.
And once those new customers tell their friends and relatives how they found your website, more people will know you made sure to make it ADA compliant. The fact that you put this effort into ensuring everyone was included will set you apart from your competitors. Therefore, making your site ADA compliant is a great way to get some positive press for your business.
On July 26, 2010 (on the anniversary of the Americans with Disabilities Act) President Obama stated that ADA accessibility must also apply to the Internet. With that declaration, the Justice Department was tasked with setting rules for ADA accessibility for the Internet and websites. Since that time, the Justice Department has formulated recommended rules for ADA website accessibility. Those rules will soon be refined and officially released in the near future. Until then, there is a set of guidelines currently in place (http://www.w3.org/WAI/WCAG20/quickref) for websites to become ADA accessible. Even with these guidelines in place, many hospitality businesses have not yet complied with the guidelines. Now is the time to begin the process of making your current website ADA accessible or to consider a new website design that is ADA accessible.
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. 
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.
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