I am wondering what are some specific questions I should keep in mind when I am comparing programming languages for use on given work projects. For instance, I am told logic programming languages like Prolog are good for natural language processing. I'm not sure why exactly; I assume it is true because experts say so, but I don't know the consideration that guides them to that conclusion. So I am looking for a simple heuristic, a checklist of questions, I can apply to evaluate programming languages and be able to explain my decisions, so that I can say "Language X is good for Y because it does Z."
The only way I know of to figure out which programming language is most appropriate for a given problem, is to know lots of programming languages. After all, if you don't know screwdrivers exist, how will you know not to use a hammer when you encounter a screw?
Unfortunately, there are thousands (maybe tens of thousands) of programming languages, so learning even a significant portion of them is just not realistic.
However, programming languages implement paradigms. And Peter van Roy's famous poster only lists about 34 of those. Although he deliberately decided to ignore several aspects, including anything related to typing, so the real number is probably higher than that. But we can expect it to be well below 100.
That's still a lot, though, but thankfully, paradigms aren't atomic either, they are composed of concepts. The poster lists about a dozen of those (again ignoring typing and a couple of other things). Significantly less than paradigms.
Learning a significant portion of concepts is entirely feasible. Once you know them, you can look at a problem and see which concepts would be useful to have to build a solution. Then you look at which paradigms contain those concepts and which languages implement those paradigms. Pick one, learn it, use it, solve the problem.
And since you already know the concepts (and thus the paradigms) the language implements, you only need to learn the syntax, not the semantics. There aren't actually that many different syntaxes in the wild (C, C++, Objective-C, Objective-C++, D, Go, Java, C#, ECMAScript, PHP, Vala and many others share a lot of syntax, for example, as do Smalltalk, Self, Newspeak and Objective-C, SML, OCaml and F#, and so on), so chances are, you'll pick that up very quickly. (Besides, with today's modern IDEs that's much less of an issue anyway.)