I'm much less worried about human piloted craft. It's very difficult to program complex decision making and discernment. The astronauts present in the first landers will have been intensively trained in how to avoid catastrophe and will likely be able to come up with solutions on the fly if unanticipated things happen. Still dangerous, but hopefully less so.
It will be much easier to land completely automatically once we have landing pads, radar tracking, and other infrastructure present on the surface. It's just hard to land a robot on an airless moon with a bunch of rocks and hills and shit everywhere.
I'm a senior software dev and have built a shitload of tools and scripts that are command line only. I've been told that I'm a really great developer, and I have a knack for figuring things out, even when there's no documentation.
For the life of me, I absolutely cannot wrap my head around frontend shit. Like, I can do markdown just fine. HTML? CSS? Any of the popular frontend UI frameworks? I just seem to have some sort of conceptual and motivational block that prevents me from figuring out how to make those accursed fucking frontends.
It's such a different form of software development. I wish I could wrap my head around it, but I've accept that I'm not ever going to be a frontend dev. I just write server side stuff and scripts. I apologize if you ever have to use my software :(