It should be possible to upgrade ki shell to some new version of Kotlin, but only with language version 1.9 or below. Unfortunately I have no time to do it myself at the moment, but if someone will volunteer, I'll gladly accept a PR.
About supporting it for LV 2.0+ - I cannot answer anything definite right now. There is an ongoing work on supporting REPL in K2, but when it will be finished and will it be available for ki shell and similar projects - I cannot foresee now.