I’ll grant that the analogy isn’t perfect. (Is this proof that all analogies involving cars are flawed, even when the situation being analogized is reversed?)
You’re still hitting at my point in your first paragraph, though. Uber’s big lie is that they’re a ride-sharing service. They’re not. They’re a taxi company, exploiting loopholes and legal gray areas to avoid having to take on any of the social, legal, or administrative obligations - and attendant expenses - that come with that distinction (while still somehow losing billions of dollars anyway). If Uber actually has to classify its drivers as employees (which I think they do, given the amount of control they exert over them), then it’s incumbent upon Uber to ensure that the service they’re offering to the public is ADA-compliant.
If Uber were just a ride-sharing platform (“Craigslist, but for hitchhiking”), then I don’t think it would be incumbent upon them to provide an ADA-compliant fleet - after all, they’re not actually providing the service, they’re just serving as an intermediary between individuals. Assuming mobile apps are subject to ADA compliance (an assumption that is greatly lacking in legal precedent, AFAIK), all Uber would need to do is ensure that their app was ADA-compliant, and they’d be in the clear.
The rules for regulating an actual ride-sharing economy under the ADA are admittedly more difficult. On the one hand, direct person-to-person transactions for services outside of a business or civil context haven’t really been subject to ADA scrutiny. On the other hand, I think the need for ADA compliance increases the closer to a business-like operation you get. So, would an actual ride-sharing economy require every driver to obtain ADA-compliant vehicles, or at least provide an acceptable level of service for disabled individuals? Maybe. As with “commercial vehicle insurance”, it’s kind of a question of intent. I don’t have to have a commercial insurance policy on my truck because I’ve driven friends (or even strangers) around town on occasion, but I would have to have it if I put a sign on the roof and started doing it as a job.
To a certain extent, the “sharing economy” illustrates the problem of corporations trying to foist the responsibility of providing critical services off onto individuals. It’s a lot more practical to require a taxi company to provide accommodation for everyone across their entire fleet than it is for every individual person to buy an ADA-compliant lift van. (Ideally, larger organizations would also pay their employees well enough that they wouldn’t need to make money renting out their apartment for a weekend or driving people around town, but that’s a different aspect of the larger and thornier problem of corporate malfeasance.)