How long has it been since you used MonoTouch? I first used it a little over a year ago: debugging over the wire worked just fine (though you can debug over a network connection), the API was only ever behind on major iOS updates (it's also not hard to call an Obj-C API from MT yourself, without waiting for them to put out a new release of MT), and all the compilation was handled by command line programs called by the MT MonoDevelop plugin - you could call them from make/Rake/whatever, should you prefer to.