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.
"I’m a couple years away from retirement and have a very limited budget and after talking to some other web developers through thumbtack I quickly realized I was not going to be able to afford a website built by anyone but myself. Then I got a response from Jean Johson of B’yond Media telling I was chosen to get my free website. Crazy, is all I can think of. Why me, and is this too good to be true. But after speaking with Jean for awhile in the phone I soon realized that I was really going to be getting an awesome e-commerce site for free. I’m over the moon and have already started gather information for them for my site. They were a God send. I can’t think of anyone I would rather do my website free or not than Byond Media and Jean Johson as my project manager. You must give them a try. I’m sure you will be as happy as I am."
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.

Your site would need to have a text only option, with all functionality accessible through a keyboard for visitors with mobility issues. Once you make these and other changes to meet ADA guidelines, your site would need to be tested by a website development company familiar with ADA compliance issues to be sure that visitors who use assistive technology such as screen readers are able to access your web content fully.
President George H.W. Bush signed the Americans with Disabilities Act into law July 26, 1990. The ADA prohibits discrimination of people with disabilities and guarantees the same opportunities as everyone else. These opportunities include employment possibilities, purchasing of goods and services and the ability to participate in State and local government programs.
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.
This past September marked the first time a judge ruled that the ADA applies even to businesses without a physical location. Scribd, an e-book subscription service is considered to provide "a place of public accommodation." Their services are not accessible to blind persons because they cannot be read with a screen reader. The judge reasoned, "Now that the Internet plays such a critical role in the personal and professional lives of Americans, excluding disabled persons from access to covered entities that use it as their principal means of reaching the public would defeat the purpose of this important civil rights legislation."
Over 10,ooo business owners were sued this year (2019) and they expect that # to increase to over 100,000 in 2020.  And these are no-joke lawsuits.  They settled for $20k - $6million, average was $50k...crippling to most small business owners, and you can't win these cases.  Unlike GDPR, the ADA law doesn't require any notice before a lawsuit can be filed for non-compliance, and it doesn't provide any time for a company to take positive or corrective action before its filed, so there's no real defense.  It's basically just a race to see who wins...the site owner that protects his or herself, or the dirty lawyer that finds them before they did.  Getting sued is a REAL risk, not the usual fake scare we usually see that disappears over time.

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The ADA is the Americans with Disabilities Act, passed almost 30 years ago in 1990. This act was originally put in motion pertaining solely to physical location. It requires establishments to provide people with disabilities easy access to various levels throughout the business. This act was set to achieve an equal experience to all people, handicapped or not.
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