But again, even if you are exactly right, it won't be too late for Uber. Either they'll be successful, and so have plenty of money, or they'll be troubled, and this business won't be nearly enough to save them. And in the meantime, it's at best a giant distraction, and at worst they smother it, as happens all the time with large-company acquisitions.
Compare with Apple. They were 3 years behind on smartwatches, 4 years behind on MP3 players, 6 on smartphones. It didn't matter, because they had skills, assets, and market power. It was better for them to wait and let others prove the market and then come in when the shape of consumer need and likely solution was clearer. I think the same would be true if Uber were a successful, stable company.
In particular, you've had to lock up your bike and still had it/parts stolen - not your problem if it's not your bike. Not being your bike also takes care of the maintenance - not your bike means it's not your problem! (I mean, don't go around trashing their bikes for the sake of it, but it means you don't have to worry about the derailleur alignment or tire/rim sizes.) There's the logistics of biking - if you go out, but take a taxi home, then you have to come back to get your bike later. Jump means you don't have to, and if you don't bike back, you can take an Uber instead.
You've definitely had a car almost kill you - likely more than once. The new protected lanes that are popping up all over the city don't make that problem go away, but it's a big step forwards.
Imagine having never experienced being almost killed by a car.
Finally, there's that whole pedaling thing. Not to be (further) presumptuous, but I'm guessing somewhere in the 10+ years, there's a stop sign that's been run. If you stop, then you have to start again. That gets old pretty quickly on any street with stop signs every block. Jump bikes being electric makes that stop being such a workout.
None of these problems are truly insurmountable - as your experience proves! There are other problems w/ bicycling that Jump doesn't solve, but Uber's bet is the kind of friction that Jump does solve, will make this purchase profitable for them, $2 for 30 mins at a time.
Finally, since Uber knows where its riders have been dropped off, it's able to use that data to move Jump bikes around the city to optimize their placement.
If you wait until something's a "sure" thing, then it's too late - the price has gone up, so there's less money to be made. The time to buy BTC was 10 years ago, not now, but if you think it's this weird sketchy thing now, 10 years ago it was E-gold 2.0.