It is not all about cost-benefit.
You say there is a difficult time transferring knowledge from other languages when they see the `unless`. That's fair.
My response to that is that, to idiomatically think in Ruby is write code that reads well, and `unless` fits that. Every language has an idiomatic way in which one thinks and reasons with the language. While there are principles that can be transferred over across languages, the way to think in that language does not necessarily transfer. The Ruby community has a heavy emphasis on creating embedded DSLs that seems natural enough to written English, and the Ruby community's style guide is written for that.
In contrast to Ruby, Python has idioms that seem to be the inverse of Ruby. The intuitions on what is good, idiomatic Ruby is counter-intuitive in Python. This even extends to the design of Ruby bundler vs. Python virtualenv/pip. As a long time Rubyist, Python rubs me the wrong way (what is intuitive in Python is counter-intuitive in Ruby) until I realized that I used to write that style of code a long time ago with Pascal.