Looking back at our paper, I think the weakest points are (1) we handwave the accelerator a bit too much (I now think laser launching is the way to go), and (2) we also handwave the retro-rockets (it is hard to scale down nuclear rockets; I think a detachable laser retro-rocket is better now). I am less concerned about planetary disassembly and building destination infrastructure: this is standard extrapolation of automation, robotics and APM.
However, our paper mostly deals with sending a civilization's seeds everywhere, it does not deal with near term space settlement. That requires a slightly different intellectual approach.
What I am doing in my book is trying to look at a "minimum viable product" - not a nice project worth doing (a la O'Neill/Bezos) but the crudest approach that can show a lower bound. Basically, we know humans can survive for years on something like the ISS. If we can show that an ISS-like system can (1) produce food and other necessities for life, (2) allow crew to mine space resources, (3) turn them into more habitat and life support material, (4) crew can thrive well enough to reproduce, and (5) this system can build more copies of itself with new crew at a faster rate than the system fails - then we have a pretty firm proof of space settlement feasibility. I suspect (1) is close to demonstration, (2) and (3) needs more work, (4) is likely a long term question that must be tested empirically, and (5) will be hard to strictly prove at present but can be made fairly plausible.
If the above minimal system is doable (and I am pretty firmly convinced it is - the hairy engineering problems are just messy engineering, rather than pushing against any limits of physics) then we can settle the solar system. Interstellar settlement requires either self-sufficient habitats that can last very long (and perhaps spread by hopping from Oort-object to Oort-object), AI-run mini-probes as in our paper, or extremely large amounts of energy for fast transport (I suspect having a Dyson sphere is a good start).