Yeah, maybe I'm just way too pessimistic, but I feel like the problems are just far too numerous and hard to solve. Even with lots of robotics - mechanical stuff breaks down, and needs to be fixed. And that fixing, even if you have a human on hand who can do it in an Earth-like environment, still requires replacement parts. Unless there's also other robots to fix the broken ones, or they can fix themselves (sounds sketchy), I just can't see it working out without lots of other advances to go with it.
The "hopping" approach like you suggest improves feasibility significantly, but of course that'd put the timeline for getting anything permanent on Mars out... probably centuries? (Unless we get some breakthrough tech which lets us build in space, or something game changing.)