One issue I continue to face in trying to get Squeak to be a viable
solution at my workplace is that Squeak does not integrate with the
common idioms of the day very well.

For instance, Squeak doesn't support SSL and HTTPS.  These are very
common protocols that just about every other major language supports.
I don't know enough about these technologies to be able to code it
myself, but surely there are people in the community who can.  My
biggest project at work is an integration with Salesforce.com via SOAP
which is currently impossible in Squeak because of the lack of HTTPS
connections.  I tried doing it in VW 7.3, but I could never get the
SOAP support worked out properly.

So, in my opinion, if we would like Smalltalk in general (and Squeak
in particular) to be easily accessible to a larger group of
developers, or even if we want it to be MORE easily accessible to its
current group of developers, these issues of "playing well in the
sandbox with other children" need to be worked out.

-- 
Jason Rogers

"Where there is no vision, the people perish..."
    Proverbs 29:18