My first experience with the JVM classpath was when I started using Clojure with zero Java experience. I quickly understood it more or less works the same as UNIX $PATH (although the devil is in the details, they are not identical), and since then I haven't really hit any issues. nodejs/npm does something similar by instead of being user set by default, it defaults to "./node_modules && ./node_modules/*/node_modules" (recursively).

Most languages deal with paths in mostly similar ways (except Go until recently). What precisely is your issues with the Java classpath that someone who have been writing Clojure code for years haven't hit yet?