I personally think that one reason why Alan lost his interrest in Squeak was partly based on the community that was too conservative and too much Smalltalk-80 oriented - while Smalltalk does not fit into his vision well already since 1976.
Then they did Etoys stuff at Disney and some other neat experiments. Then Alan moved on to 3D shared environments[1] and later to recreating personal computing in 20K lines of code[2]. The idea was to build it on top of Ian Piumarta's COLA[3][4] but to get something out the door they ended up using a stripped down version of Squeak instead. So moving on from Squeak is harder than Alan hoped.
[1] https://en.wikipedia.org/wiki/Croquet_OS
[2] http://www.vpri.org/pdf/tr2012001_steps.pdf