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.

For discussion’s sake – while I don’t know the specific nature of your videos, my guess is that they might be demonstrating various techniques or other content in which simply hearing the audio of the video wouldn’t deliver the full context of the content. If making that content accessible is something you’d want to do, you’d likely want to start with a written description of what takes place in the video. Beyond that, high contrast vector images or diagrams showcasing specific parts of the technique would certainly help.

Do all websites have to be ADA compliant? Does yours? Though the legal definitions are somewhat unclear, it is clear that inaccessibility invites legal action and misgivings from customers. Web accessibility does not have to be complex, and it may not take much to test your site and make it accessible. Take web accessibility step by step and you can avoid stressful lawsuits, and invite all patrons to your website.
I was educated at the Illinois Institute of Art in Chicago and have over decade of graphic design experience developing t-shirts, posters, flyers, illustrations, web graphics, and many more. All of my work delivers on creating high quality images filled with detail and color. My belief in establishing a good relationship as well as excellent communication with each of my clients helps me produce the professional work they are looking for. My ambitious nature and need to create fuels my drive to always deliver the best for my clients.
If your hotel used responsive web design when creating your online marketing strategies, you’re already meeting many of the ADA compliant regulations for hotel websites. You will still need to make some changes, but you definitely have a head start. Making the changes now, before your business is the target of a lawsuit or government action, makes good business sense.   
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The fastest, most certain way to be sure your website is in compliance is to contact a qualified web design agency and have them perform an audit of all your online properties. Make sure you interview the agency thoroughly first, as not all agencies are up to speed on ADA website compliance rules. A qualified web design firm will be able to identify any violations of ADA Website Compliance and outline a plan for updating your online content and properties. 
For close to seven years, since July of 2010, the United States Department of Justice (DOJ) has talked about issuing regulations specifically about web accessibility. At that time the US Department of Justice (DOJ) began developing accessibility guidelines for public websites under Title III of the Americans with Disabilities Act (ADA). On December 26, 2017, the Department announced that those regulations were officially withdrawn.
The Department of Justice may file lawsuits in federal court to enforce the ADA Compliance, and courts may order compensatory damages and back pay to remedy discrimination if the Department prevails. Under title III, the Department of Justice may also obtain civil penalties of up to $55,000 for the first violation and $110,000 for any subsequent violation of ADA Compliance.
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!

Jeremy I am an artist and designer. The business I would like to have a website for is painting pet portraits. I also paint them with their owners, kids, etc. The reservations I have about the (template choice) website plans is that none of the templates I have seen show what I do well enough. Is there a site where I can setup or design my own homepage image without using a prescribed template?

While legal considerations might be your biggest worry, making your site more accessible is simply good customer service. More than 39 million Americans are blind and another 246 million have "low vision," Another one million are deaf in the U.S. Add to that people with mobility issues that prevent them from using their hands and that's a huge portion of the country's buying power.
Various courts around America have ruled that commercial websites are places of public accommodation and thus subject to ADA rules. Other cases have concluded that websites are bound by ADA regulations if there is a close “nexus” between the site and a physical location, the most famous example being the ruling against the Winn-Dixie supermarket chain for not making its site accessible to users with low vision. Other courts have decided that the ADA as written simply does not offer any protections for online users. With no overarching federal rules in place, it’s difficult to make a definitive statement about whether or not any given website is governed by ADA accessibility rules.

Government Code §11546.7 – The requirement that state agency heads certify, every two years, that their agency’s website meets the Web Content Accessibility Guidelines, Version 2.0 or a subsequent version, at Level AA or higher, and the requirements of Sections 11135 and 7405 of the Government Code. Created by AB 434 (Baker, Chapter 780, Statutes of 2017), and sometimes referred to as AB 434.
In some circumstances, longer and more detailed text will be necessary to convey the same meaningful information that other visitors to the website can see. For example, a map showing the locations of neighborhood branches of a city library needs a tag with much more information in text format. In that instance, where the map conveys the locations of several facilities, add a “longdesc” tag that includes a text equivalent description of each location shown on the map – e.g., “City Center Library, 433 N. Main Street, located on North Main Street between 4th Avenue and 5th Avenue.”
The WCAG guidelines were updated from version 2.0 to 2.1 in June 2018. The updates in 2.1 cover changes in technology that have occurred since the previous version, and also address areas that were underrepresented in 2.0. What does this mean for you? Not a lot right now. The compliance level targeted is still WCAG 2.0 Level AA, and the 2.1 success criteria are in addition to those already existing in 2.0.
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.
Luckily, the international nonprofit World Wide Web Consortium (W3C) brings together smart people who develop open standards to ensure the long-term growth of the Web. They produce recommendations for making websites fair and equally accessible for the highest number of people possible. Their Web Content Accessibility Guidelines (WCAG) 2.1 offer clear guidance for web developers to achieve ADA compliance.
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If you use outside resources for your web needs, or have a dedicated web person or company, call them immediately. If you have a department or staff, even better. But— if you are working on your own, you would do yourself and your business a favor to contact a reputable web developer to discuss how to make your site accessible and avoid possible lawsuits. The older your website, the more likely it is that it is NOT compliant. Take action now!
Do all websites have to be ADA compliant? Does yours? Though the legal definitions are somewhat unclear, it is clear that inaccessibility invites legal action and misgivings from customers. Web accessibility does not have to be complex, and it may not take much to test your site and make it accessible. Take web accessibility step by step and you can avoid stressful lawsuits, and invite all patrons to your website.

HTML tags – specific instructions understood by a web browser or screen reader. One type of HTML tag, called an “alt” tag (short for “alternative text”), is used to provide brief text descriptions of images that screen readers can understand and speak. Another type of HTML tag, called a “longdesc” tag (short for “long description”), is used to provide long text descriptions that can be spoken by screen readers.