To answer your question about the amount of work required to navigate through datatokens: the reason there are so many steps is because datatokebs don’t have strict types, but they exist inside of an environment which does have strict types.
Datatokens are a concept that straddle across multiple different places - udon graph compiler, U# compiler, json input data, udon assembly, and C#. The only way to do that is to support the broadest possible interpretation of types. As not all environments have strict typing, it is impossible for datatokens themselves to have strict types.
However…. U# is powerful enough that you absolutely have all the tools you need to add strict types on top of datatokens, but it is something that must exist inside of U#, which is firmly outside the realm of what datatokens are capable of doing. Instead, it is up to you to create those definitions and mappings.
One way to do this is with a darkclass generation tool: Improved U# DarkClass (Generation tool available) - チカラの技術
This tool allows you to interact with objects that appear to be strictly typed classes, but under the hood it ends up creating a set of helper libraries for your context-specific set of classes that access the datatokens for you, and exposes convenient access points.
Alternatively, if you are interested in diving into things a bit more manually, you can also use the same underlying concept to create custom classes that inherit from datalist and static extension methods.
Regardless of the path you take, the end result is the same - create a helper library which exists to handle navigating datatokens and exposing operations to your strongly typed c# environment.
It’s worth mentioning that I would only recommend doing this if you feel strongly that you want to uphold a strongly typed c# environment. Some people who come from places like JavaScript or Python are perfectly happy operating with strings and loose types. There is no right answer, its just different paradigms. In this case, if you feel strongly that you want strong typing and clean, simple syntax, you do have to put the work in to establish that for yourself