I'm probably one of the few who get your "CLI" comment and wish everything started with en, conf t, router BGP (ASN)/OSPF/EIGRP, etc. Show ip route is also a go to in enable mode.
Anyway, I think you've worked things out pretty well. Implementation without a lab (I'm assuming SSH doesn't have a dedicated lab) is just asking for problems, but as long as they're visual and not functional, it's okay. It's not like this is a hospital environment where cranky people like me are going to get the wrong infusion.
That being said, I think the one thing I'd change is the color of the new alerts. For people who have spent too much time hunched, and squinting, over a screen, the difference between the grey and white isn't a whole lot. Perhaps some flair with a light pinkish or yellow tone would be nice.
Just a thought.....
Oh......I love CLI, but way back when, I loved menu driven. Make sure you stay up on more policy driven interfaces, but you probably already knew that.