I loved working with Smalltalk as a language, and developing inside the fully integrated VM. It's my fondest development experience to date.
I really didn't love deploying Smalltalk applications and even collaborating was more difficult than file based languages/systems. Deployments (at the time) were a practice of shipping the image to the servers that needed to run. There literally is no (separate) "runtime" it's all in the image. This thing got bulky real quick.
I haven't touched Smalltalk in a while, so maybe (hopefully?) things have improved and deployments are no longer a problem.