I really like The Mythical Man-Month by Fred Brooks. It’s originally from 1975, based on his experience in managing a team that wrote the operating system for a series of IBM computers. So it doesn’t talk about modern tooling. But I do like the way it gives the lay of the land, so to speak. Lots of interesting ideas, and quite a lot of wonderful illustrations and diagrams too :)
I think one of the motivations for having separate modes like this, with (some) separate registers for each, is to reduce the time taken to switch contexts between modes. If they didn’t have separate registers, the data in the user mode registers would have to be saved somewhere when making a switch into kernel mode, and then copied back again when switching back to user mode.