The type of operating system and hosting doesn’t matter much for design, but the platform is a factor. For instance, if you need a WordPress theme, the designer must work with WordPress themes and customize them in a way that a developer can feasibly code in CSS or JavaScript on the front end. If you use another CMS, the developer must work with those elements. Most designers specialize in specific platforms, so review their portfolios and experience for specific platforms before you invite them to bid on your project.
Case law has been the most helpful in illuminating the implications of the ADA for websites.There have been lawsuits involving companies like Expedia, Hotels.com, Southwest Airlines, and Target as defendants and primarily featuring accessibility organizations as plaintiffs. These cases had mixed results, but each helped clarify the ADA's jurisdiction on the web. 
Web designers are must-have for any site owner. Whether you’re building a new site or your existing design needs a refresh, you’ll need a good designer that can match your business style with the right layout, color scheme, and user interface (UI). Like fashion, web design trends change frequently so you need a designer who understands the market, UI, and user experience (UX) design, and who knows how to use this to make your site attractive and easy to navigate.
As I mentioned above, under each WCAG 2.1 principle is a list of guidelines, and under each guideline are compliance standards, with techniques and failure examples at each level. Some guidelines include only Level A items; others include items for multiple levels of conformance, building from A to AAA. At each stage, you can easily see what more you would need to do to reach Level AA or AAA. In this way, many websites include elements at multiple levels of accessibility.
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.
The Federal Communications Commission (FCC) enforces regulations covering telecommunication services. Title IV of the ADA covers telephone and television access for people with hearing and speech disabilities. It requires telephone and Internet companies to provide a nationwide system of telecommunications relay services that allow people with hearing and speech disabilities to communicate over the telephone.
If you think you have been discriminated against in employment on the basis of disability after July 26, 1992, you should contact the U.S. Equal Employment Opportunity Commission. A charge of discrimination generally must be filed within 180 days of the alleged discrimination. You may have up to 300 days to file a charge if there is a State or local law that provides relief for discrimination on the basis of disability. However, to protect your rights, it is best to contact EEOC promptly if discrimination is suspected.

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Poorly designed websites can create unnecessary barriers for people with disabilities, just as poorly designed buildings prevent some people with disabilities from entering. Access problems often occur because website designers mistakenly assume that everyone sees and accesses a webpage in the same way. This mistaken assumption can frustrate assistive technologies and their users. Accessible website design recognizes these differences and does not require people to see, hear, or use a standard mouse in order to access the information and services provided.
Aloha Tatiana! I wish your questions had straightforward easy answers – and if you are government funded it kind of is. (See here: https://www.ada.gov/websites2_prnt.pdf) if you are not government funded, this is something that is currently being debated in the legal system. That being said, the WCAG 2.0 guidelines are a good set of guidelines to help protect yourself if you feel you should. (You can see more on WCAG here: https://www.yokoco.com/find-out-how-to-make-your-website-compliant/)
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