My first impression: the fonts are way too small.

The official image with welcome files etc is an advertise. It tries to 
catch eyeballs and to generate interest. For good reason ads are using 
big fonts. Someone new to squeak is forced to read lengthy readme files 
written in an absolutely distracting font.

Will the newbie be encouraged to do so?

Squeak is marketing itself definetely not well this way.

Lets assume the newbie gives it nonetheless a try and wants to find out 
ie how to make fonts bigger, how to change the look and feel (-: how to 
start programming. What happens next? Newbie opens up window after 
window and soon he realizes:

YOU CAN'T SWITCH BETWEEN WINDOWS!

The only way for him to do so, will be closing or dragging all windows 
which are hiding what he is looking for right now.

There is no windows taskbar.

At least on a german pc keyboard the ctrl/cmd-$\ does not cycle through 
the windows and even if newbie finds out about 'find window' and if $\ 
would work, the windows handling were much too inconvenient to compete 
with Windows, KDE and the like. This holds true especially, because 
Squeak likes to spawn windows instead of reusing open browsers - 
compare it to the Dolphin browser or VisualSmalltalk with its viewzoom.

Especially a newcomer is drawning in windows, because he has not 
internalized the classhierarchy and all the other info an oldtime 
squeaker knows. 

Newbie might think: They invented the window engine 30 years ago and 
now they forgot the steering wheel?

Sad, but at this point the journey into squeakland ends.

I know it is too late for a change in 3.2 but this is the single most
disappointing item which let me try 2.6, 2.8 and 3.0 each for about 10 
minutes before forgetting about Squeak for the next long timespan. It 
was only Microsoft with its increasing impudence which let my try 
harder this time. 

Martin