We have visuals
This is the first screenshot I have to show of the hacksim game thing; massively work in progress, this shows that while the game is heavily command-line based, there will at the very least be a fancy globe for traceroute etc.
Making procedurally generated yet interesting content will be difficult. Adding a number of tailored storylines, and attaching these to semi-random servers is probably the way to go.
So far, I have been thinking about somehow gathering keywords when a server is requested. This way, google.com would be a search engine, nasa.gov a space agency, cern.ch a scientific research facility and so on. For this to be viable, servers should be put into predefined and -programmed categories.
Colours!
In this way, storylines could be specified not per-server (or per-organisation), but rather in a server-agnostic way. Imagine a generated scenario with you working for the KGB to bring down FBI!
Simple single- or few-hacks jobs should be plentiful, and available for or against most servers. And all but a select few servers (used by the game) should be hackable as well.
This will take a while. For now, enjoy the (rather bland) screenshots.