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> For more complex cases I find myself wishing I could just turn Typescript into some kind of schema validation for JSON.

Not sure if this is what you're looking for, and whether it's powerful and expressive enough for your use case, but you can use typescript-json-schema¹ for this, and validate with eg ajv.

¹https://github.com/YousefED/typescript-json-schema

I like JSON5 for similar reasons. I specifically like the addition of comments, trailing commas, and keys without quotes.

Also needed is string concatenation. One line strings are very limiting.

I've struggled with this in Java recently and at first I used Jankson which supports the complete JSON5 spec, but later we figured out we could configure the standard Jackson JSON package to accept the things we actually need and actually use.

There's libraries that let you define a schema programmatically, and then infer the types.

https://github.com/sinclairzx81/typebox