At an emotional level I get this and can sympathize. But at a rational level... what would be shortcomings of a Lisp programming environment or Smalltalk image, versus Win/Mac/*nix?

Perhaps I had better specify: apart from software ecosystem support.

(I see one great thread talking about downsides of image-based(as in, Smalltalk image) on related @ https://news.ycombinator.com/item?id=34300806#34302095)