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.
“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.” (Read full article.)
What do you want your website to look like? Consider websites that are similar to the one you’d like to build, ideally in the same industry or serving similar types of customers. Build a set of examples of types of pages, design aspects, and website features that you can hand off to the web designer — the person you hire should have experience creating websites with the features you want. If they don’t have the right skill set, they’re not the right pro for you.

The words in the tag should be more than a description. They should provide a text equivalent of the image. In other words, the tag should include the same meaningful information that other users obtain by looking at the image. In the example of the mayor’s picture, adding an “alt” tag with the words “Photograph of Mayor Jane Smith” provides a meaningful description.

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