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.
-compensation for valuables in the bag
-compensation for software/files/etc
-compensation for time wasted
-compensation for di-stress caused
-compensation for tickets & hotel (if I get this right, the "victim" had to fly in for the court)
The Uber may had to cough-up 6-8-10k, the lawyer would get 2-4k for 2 hours worth of work and all would be happy
He could go to regular court to claim a larger amount, but that's a more involved and lengthy process.
Agree on the mistake of giving Uber all the info. The guy was trusting Uber not to be as scummy as they ended up being. I'm sure he has learned his lesson and next time regardless of company, especially once lawsuit stuff has come into play, will do what you said:
> What he should have done was say "we can discuss this in court, or you can make me whole now and avoid that," and NOTHING else.