I would agree that a lot has been done, and believe me... I wasn't dumping on Uber. I still use the app myself. I'm just saying from a practical viewpoint, it's a serious consideration to be made if someone is moving to a new job.
Personally, when I joined, I made a similar bet based on what I could gather about its growth trajectory at the time and a belief that corporate scandals eventually get closure.
I'm a bit on the risk-tolerant side, so RSUs two years ago with IPO rumors flying around and bad public perception seemed like good timing. With the current landscape, I think Uber is less risky than two years ago, and I even agree that Square might be more attractive to a more risk-averse person, but yeah, at the end of day, I think it still boils down to personal preferences/risk tolerance.