You probably won't have to check your site with all of the available evaluation tools out there, but it is a good idea to do so for the most common web browsers. Just as accessibility software makes it easier for people with disabilities to navigate the Internet, these tools make it easier for developers to ensure accessibility from the start. When you think you've mastered it, go back through the Section 508 compliance checklist to ensure you've met every goal.
Hey OB – Disclaimer – none of this is legal advice and you’d want to check with a lawyer to know if you’re at risk for any action if you’re not ADA compliant. Based on what we’ve seen if you don’t have a physical retail or service location, and you don’t receive any funding from the government you likely aren’t required to have a website that would be considered compliant. Some people expect that to change in the next few years, but that’s what we know for now. Let us know if you have more questions or would like to test your site.

Since March 15, 2012, ADA compliance with the 2010 Standards will be required for new construction and alterations. In the period between September 15, 2010 and March 15, 2012, covered entities may choose between the 1991 Standards ADA Compliance (without the elevator exemption for Title II facilities), the Uniform Federal Accessibility Standards (Title II facilities only), and the 2010 Standards ADA Compliance.

The ADA itself holds different organizations to more/less stringent standards based on a host of factors, government funding being a major one. Government agencies themselves are usually held to the most severe standards. That said, while ADA has adopted WCAG as the defacto standard, from what I’ve seen it appears they’re going with AA compliance as the most reliable one. That said, we’ve done work with some organizations who’ve chosen to comply with AAA in an effort to be as buttoned up as possible from an accessibility and experiential perspective. We’ve also worked with some who have tighter budgers and aim for level A compliance and have a more “react and repair” mindset when they discover anything in their site that is giving someone hardship from an accessibilirt standpoint.
Another important consideration is that the ADA does not allow businesses to simply provide an alternative such as a phone number. Lastly, include accessibility issues as part of your website and mobile strategy. When new technologies are implemented or pages added, part of the process should include the implications for persons with disabilities. 
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.

I own a medical practice in California with 5 employees. Since I have under 15 employees am I exempt from needing to have my website comply with the ADA? I know that my physical practice is exempt from ADA policies regarding employment (under 15) but I don’t know if that extends to websites. My website is not an important part of my practice and I don’t really want to sink any funds into it if I don’t need to.