Having settled on bash + awk, the OP approach makes perfect sense. But it is tedious. If written in python we could "import typer", write a one-line function signature, and get {parsing, diagnostics, --help} "for free".
The fundamental issue is we chose an inappropriate calendar representation. Yes, we could finesse it with subkeys for sorting. But it would be far more sensible to parse out something like a dt.datetime or even an ISO string.