Usability comes second in the list of complains from my acquaintances, which I tried to Squeak-e-vangelize. The first obstacle is obviously no edit-compile-cycle but we ain't gonna get it (it makes no sense at all in Squeak).
At this point I'm just puzzled. Why would people so deeply in love with the edit-compile-cycle they find it hard to live without it even consider Smalltalk (or Lisp, for that matter) in the first place ? I'm lost. Maybe you should start by selecting a bit more carefully the people you want to Squeak-e-vangelize (half-kidding here, no offense intended).
the programmers not so familiar with Squeak definitively have to understand the principle behind the workspace, transcript, class browser, saving an image, etc. Nonetheless, the sense of being lost in this new but exciting environment would not repulse them if only they could find familiar elements.
Or, at the contrary: let them experience a big shock that wipes out their preconceived ideas about programming. Trying to help them avoid that shock may actually make thing more difficult for them in the long term. They have to grok that Smalltalk *is* different.
Stef