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.
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.
Aside from attempting to compliant for compliance’s sake, having an ADA accessible website can improve the overall user experience and site traffic. An ADA compliant site can increase your target audience (by making it easy for those with disabilities to navigate around), improve your SEO efforts (by helping search engines to more easily crawl your pages and content), and help your overall reputation.
Many people with disabilities use assistive technology that enables them to use computers. Some assistive technology involves separate computer programs or devices, such as screen readers, text enlargement software, and computer programs that enable people to control the computer with their voice. Other assistive technology is built into computer operating systems. For example, basic accessibility features in computer operating systems enable some people with low vision to see computer displays by simply adjusting color schemes, contrast settings, and font sizes. Operating systems enable people with limited manual dexterity to move the mouse pointer using key strokes instead of a standard mouse. Many other types of assistive technology are available, and more are still being developed.
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. 
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.
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...
For most businesses, the need for ADA web compliance means they will need to make at least some adjustments to all of their online marketing strategies. For instance, if your company provides tax preparation services, all of the tax forms you provide for customers to download would need to meet accessibility standards. Any online tax preparation services that you offer would also need to be configured so they meet ADA standards, as would your mobile app.
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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. 
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