The two major annoyances to me in Squeak are that the above things
aren't possible. The latter one is a real PITA, the other would be
extremely nice-to-have. I've been digging (but only a bit), but didn't
find anything readily available - is there something? Would it be hard
to implement?

For clarity:
- pass window activation click: if you click on a window, the window is
  activated and the click is passed on for further processing. So with a
  single click, you activate the window and press a button, or start
  scrolling, whatever;
- focus follows mouse: the window under the mouse is active, with
  possibly a slight delay. From this follows auto-raise, where the
  active window is automatically brought to the foreground after a
  configurable time interval.
I've been working in Squeak most of my time during the last couple of
months, and I'm still not used to the fact that the event processing
system 'eats' the window activation click.

-- 
Cees de Groot               http://www.tric.nl     <cg at tric.nl>
tric, the new way           helpdesk/ticketing software, VoIP/CTI, 
                            web applications, custom development