We gave up on Squeak [in 2001] because of issues with its performance, stability, poor development tools, non-support for team programming, non-support for object databases and CORBA ORBs, and the confusion about its multimedia I/O facilities.
Reading that reminds me of just how far Squeak has come in the last two years - not in terms of the really cool stuff, like Morphic or the self-hosted VM, but in terms of the practical stuff that lets people get real work done. Performance is totally adequate now - anything above about 500Mhz and Morphic (finally) stops feeling sluggish. Stability? I've had server apps running for well over a year with no hiccups. Development tools? Squeak now has the Refactoring Browser, the gold standard of Smalltalk dev tools. Team programming? There are a few options out there, but Monticello in particular is starting to kick some ass, IMHO. Object databases? There's a port of the well-respected OmniBase, an all-Squeak GemStone-like OODB called Magma, MinneStore... but ok, still no CORBA.
Squeak has a long way to go, particularly in terms of documentation and UI support suitable for (non-web-based) business apps, but it's no toy. I've been helping my clients use it commercially for the last two years, and intend to keep doing so for years to come.