The "medallion" system has its own problems, usually relating to monopoly power. The debt issue you mentioned is an example of that. However, Uber (and similar

The "medallion" system has its own problems, usually relating to monopoly power. The debt issue you mentioned is an example of that. However, Uber (and similar businesses like airbnb) are really little more than the exploitation of legal loopholes to bypass the usual costs of employment law and industry-specific regulations. Socializing expenses is always profitable, and its easy to beat existing players if you aren't paying the same expenses. Regarding job security, normal employees at least have a collection of legal protections that cover the employer-employee relationship. It's obviously not going to stop every type of abuse, but it's better than nothing. Some jurisdictions have started to catch up and force Uber et al to act properly, but as usual law is (very) slow to update.