Give Clojure a go.
It’s a modern variant of lisp that runs on the JVM and has deep interoperability with Java, so you can leverage your existing knowledge of Java libraries.
But as it’s a lisp, it will have you thinking about problems in a very different way.
Linux doesn’t really know about drives, it knows about partitions and mount points.
Obviously this is a simplification, but in general it’s close enough. It also could well be your problem - timeshift doesn’t know or care that /boot is on the same physical drive as the rest of your system: if it’s a different partition, it’s separate.