Taking extreme sports and jobs into consideration, and the fact that space is considered more and more as a lucrative destination for profit making, I think that human beings will be the first to do most of the ground breaking work. Virgin Galactic, the SpaceX moon flyby, etc. are meant for tourists, hence the different approach to absolute safety. I think the public's acceptance of the dangers of space, and the thrill/benefits of confronting them will come before we get to the point of having the necessary robot tech to make significant progress without humans on site. Then again if you consider things like Andy Weir's The Martian you realise that's a likely scenario of the kind of spending that might happen in the case of a stranded astronaut after a disaster, sending more afterwards would still be a financial decision rather than one of public opinion regarding safety however, and in my opinion the tech and financial support for these sorts of missions is going to be up to it in a few years.
Yeah, someone always brings up mining, Alaskan crabbing (was it crabbing?), etc. Anyway sure, 4 years ago we had the same conversation... I guess someday greed might overcome the risk. Still, the lawsuits over loved ones could get expensive.
My observation is that we can start immediately with attainable goals, at a cost we'll likely accept, with no risk of human life, and with immediate economic and technological benefits.
In the meantime, we've lost 4 years... with another decade more with no real goal.
My suggestion makes forward progress every year. At some point, sending humans to Mars, for example, becomes a small inexpensive step, rather than a giant costly leap.