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I'm not a fan of the whole "late-stage capitalism" meme, but I think that perfectly describes your complaint here.

The ideal approach is two pronged, you raise the standard which benefits society as a whole and increase the social safety net to take care of those few lost in transition.

The same principle applies to a wide variety of economic changes from increased labor regulations, to housing, to free trade, to automation. Your complaint here is mainly that we haven't followed through on protecting those caught in transition. We shouldn't fall into the trap of mistaking that for a valid criticism against raising the societal standard.

My point is that it's impossible for us to keep up and fix everyone's problem for them. We need to empower people to make their own choices. That's the best way to help.

And my point is that many times a decision made out of desperation is not really a decision at all. We should empower people so that they truly have a choice on some of these issues.

There has to be a line somewhere, though, right? We don’t want people to be able sign away their labor for the next X years and accidentally reinvent indentured servitude, for example.

Yes, definitely. I would view that as restricting choice.

I think the best way to increase wages is more and more jobs so that workers have bargaining power. I've used Uber as a fall-back and it dramatically increases my bargaining power.

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