I'm finding that it really depends heavily on the domain I'm working in. Roughly speaking, if I'm dealing with "business problems" type stuff - grab data, report on it, keep a paper trail, etc. - I want a very loose and flexible programming environment with a REPL and dynamic typing and all that. Python, for example, treats me very well when I'm wearing my "data scientist" hat.

OTOH, when I'm doing more "building infrastructure" type work - implementing a data store, writing a compiler or interpreter, stuff like that - I start getting more interested in rigidity and formality. Static languages treat me well in these situations. The more rigid, the better - I'll prefer Scala to Java, for example, specifically because it gives me more tools in the type safety department.