Last week, I did some research about adding support for Zoltan's new Soft Debugger to MonoVS and / or MDB.
After playing around with it a little bit and looking at MonoDevelop's implementation, I decided to take a different path and kill two birds with one stone - by adding support to the debugger itself. Since this debugger already has a pretty good client / server abstraction, things are working out pretty well so far - I'm basically creating a new soft debugger "backend" and provide a new 'Language'.
This means we will not only be able to use the current cli debugger on the iPhone, but also get the MonoVS integration at no cost.
At the moment, I already got some very basic single-stepping working - we use some quick hack to stop on the first line of Main(), and then you can do some stepping. My next challenge is implementing the type system and then adding support for breakpoints.