> The guy only got $4K. Retaining a lawyer for just that amount wouldn't be worth it, would it? I have no clue how small claims works and how likely it is to have attorney fees be included if you win like you mentioned. The guy had to fly back to Boston again for the second time around. He'd also likely have spent some money in Boston like getting around. None of that was included in the final amount either. I'm not sure if a lawyer or someone more in the know how of how small claims/courts work would have been able to get it. And even if you can, how easy is it to get it.
It can be worth it, especially if - as OP mentioned - part of his goal was to prove his case to Uber, not so much to specifically recover the money. He didn't necessarily need an incredible A++ 10/10 lawyer, just somebody decent who could devote a couple hours to advising him and act as a go-between for settlement negotiations.
Having a lawyer levels you up in the eyes of court systems and corporations both. Is it perfectly worth it? Not necessarily. Is it very good advice for people considering any kind of legal action? I think so.