McMurdo on the Moon is entirely possible and I think there's a good chance we'll see it. This would get us started trying to live elsewhere and we'd start learning how to deal with the challenges. We'd also find out about the challenges we don't know.
See also my comment here: https://news.ycombinator.com/item?id=15736225 "... So where is a key area of research that should be a priority among NASA and Billionaires, but is not heavily pursued? The issue is what to do in space once you have gotten there. Because if there is a reason to be in space, then people and collectives will work to get there. And the reality is, that right now, if we could get there, there is nothing to do there short of look around and come back. And if that were the case, Space would not deserve much more investment than say tourism to Mt. Everest. The reality is that we don't know how to support human life in space -- in large part because we have only spent a pittance on thinking about that issue systematically compared to the issues of CATS and Planetary Exploration. Frankly, while we support human life on earth, we have very little meta-knowledge formally about how to do even that. And, most of figuring out how to support human life in space at a nuts and bolts level requires non-sexy activities like sitting around and staring out the window, talking, sending emails, building databases, building software tools, building some small physical prototypes on tabletops and outdoors, and just plain thinking (the hard stuff). This is all the preparation needed for the spiritual voyage into the (physical) heavens. Biosphere II was an excellent start in some ways, although the science mission was a bit dodgy at first and it seems Columbia (the recipient) seems about to abandon that effort for cost reasons --- and in any case, Biosphere II focuses on the wrong question -- we know biospheres can work and replicate (although scale is an issue) -- what we don't know is how to replicate the mechanical infrastructure (e.g. glass pane making machinery) behind them. A lot more money has gone into studying ecosystem food webs than industrial ecologies of pipe webs and assembly line webs (and frankly, a lot of people don't want their "proprietary" manufacturing processes studied or gossiped about by academics.) ..."
Maybe in 50 years the Moon can be colonized by machines, but for humans if they really want to experiment with self sufficiency, they can try building Biosphere 3 in the Sahara and see if they can survive for a few weeks without constant support from the outside.
https://en.wikipedia.org/wiki/Biosphere_2