The ADA statute identifies who is a person with a disability, who has obligations under the ADA, general non-discrimination requirements and other basic obligations. It delegates fleshing out those obligations to federal agencies. The agencies issue regulations and design standards. The regulations have the details on the rights of people with disabilities and responsibilities of employers, state and local governments, transportation providers, businesses and non-profit organizations. The design standards specify how many entrances need to be accessible, how many toilet rooms and the design for those elements.  To know what the ADA requires, you need to read the law, regulations and design standards.  
Title II applies to public transportation provided by public entities through regulations by the U.S. Department of Transportation. It includes the National Railroad Passenger Corporation (Amtrak), along with all other commuter authorities. This section requires the provision of paratransit services by public entities that provide fixed-route services. ADA also sets minimum requirements for space layout in order to facilitate wheelchair securement on public transport.[20]
Hey Casey, this is one of the areas where things get a little weird because the W3 doesn’t actually have any say over the ADA guidelines, it is more than the ADA guidelines adopted the WCAG 2.0 guidelines as just that, a guideline to help. As far as I know, the tool you’ve linked to hasn’t been used in any judgements I’m aware of. Usually when it comes down to making a decision on if something is/isn’t compliant they have people use the actual PAWS tools and show what elements do/don’t work as intended or are otherwise inaccessible. Hope this helps!
ADA compliance isn’t a set-it-and-forget-it thing. Compliance standards must be followed and will evolve just as your website does. There are guidelines all website contributors must know to stay within ADA guidelines. It is generally not burdensome but it does require some web managers to change their workflows. For example, loading images up to your ecommerce site will always need some of that alternative text (alt tags) mentioned above.

The debate over the Americans with Disabilities Act led some religious groups to take opposite positions.[32] The Association of Christian Schools International, opposed the ADA in its original form.[33] primarily because the ADA labeled religious institutions "public accommodations", and thus would have required churches to make costly structural changes to ensure access for all.[34] The cost argument advanced by ACSI and others prevailed in keeping religious institutions from being labeled as "public accommodations".[24]
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.