Just as a point of order. You offer no case for Pulumi and your one actual discussion of the semantics is misplaced as it deals with if expressions, not statements. Stratified ifs that occur at the non-recursive areas of the language are usually not a problem for these change management systems.
I'm not offering a case for or against either, to be clear - and neither are you - indeed you went so far as to say effectively you wouldn't even bother considering the semantics since they _must_ be awful.
The semantics of the Pulumi runtime are probably fine, but the semantics of the DSL layer that preceeds that when mixed with the sensible semantics of the Pulumi runtime are a recipe for disaster. This is based on my extensive experience with declarative DSLs in imperative languages. The impedance mismatch is high. Nothing to do with Pulumi's internal state management, but it's beholden to javascript.