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.
Web accessibility addresses the needs of every website visitor to achieve an optimal level of usability and ADA compliance. Many people browsing the web have a permanent disability (visual, mobility or neurological impairment), or a temporary impairment such as a broken arm, broken or lost eyeglasses, and so on. Many baby boomers have aging-related issues that make using the web more challenging, and they’re not alone–about 20% of the U.S. population has an identified disability.
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. 
I am struggling with this right now. Alt text, captions, audio (read to me) options are good. I work with an accounting software app that redesigned its palette to red, black, and gray. No green to signify income. Made no sense to me and their gray text (also very skinny sans serif) made reading many nav bars difficult. Some URLs are accessible from the build-out, but the DIY sites often don't have the same capacity. As with secure sites, I think google will be downgrading those sites with little or no compliance or accessibility add-ons.
The Department of Justice (DOJ) has specifically stated in rulings that websites should be designed so they are accessible to individuals who have vision, hearing, and physical disabilities. There’s a growing body of case law where the DOJ required companies to provide an ADA compliant website and levied hefty penalties when sites failed to measure up.
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.
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.
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Many government services and activities are also provided on websites because the public is able to participate in them at any time of day and without the assistance of government personnel. Many government websites offer a low cost, quick, and convenient way of filing tax returns, paying bills, renewing licenses, signing up for programs, applying for permits or funding, submitting job applications, and performing a wide variety of other activities.

Being one-third of the way into 2019, we opted to follow up on the 2018 discussion we had regarding ADA Website Compliance. Per last year, making sure your website is ADA compliant is significant in offering an equal opportunity for everyone to experience the products and/or services your business offers. An ADA compliant website also help prevent lawsuits and potential government action.
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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