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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.
WCAG guidelines break accessibility issues down into three levels. Level A issues are the most urgent and include problems that can severely limit a disabled visitor’s ability to navigate or use the website. Level AA issues tend to be more rooted in functionality, addressing areas where improvement is needed to give disabled users the full experience of a site. (Level AA is considered the target standard for most commercial websites.) Level AAA issues are the highest standard, fine-tuning and expanding on issues identified as Level A and AA. While it is an excellent goal, full Level AAA compliance is likely beyond the reach of most websites.
In an August 2016 case involving the University of California Berkeley, the DOJ ruled that the public university was in violation of ADA Title II (similar to Title III but it instead applies to government organizations) because their YouTube channel’s videos didn’t include captions for hearing impaired visitors. The DOJ found this to violate the ADA as deaf users did not have equal access to the online content.
There are many companies out there who claim they can bring your website up to code in as little as two days. This is simply not possible. It takes going through every page on your website and bringing each variable up to code on that page. It’s not simply a magic button that you press. This could take a single developer many hours if you have a decently sized website, hence the hefty price tag to bring sites up to code.

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.
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