So if I have a type `User|undefined`, testing `if (user === undefined || user === null)` is pointless, as `null` is not part of that type. It would be different if it were. Similarly, it makes no sense to test a variable of `User` type for value `false`, like it would if the type were `User|boolean`, or even `User|false` which you can do in TypeScript (not that you should). So `if (variable)` is still bad (ok for booleans, tolerable for some types but better avoided). You only test for what the variable can contain.
Some types you encounter are `T|null` - mostly DOM things (e.g. the return value of getElementById), but some JSON stuff as well like you said. Even though a lot of JSON just has optional properties instead, which for all intents and purposes work like `|undefined` when reading them.
From my experience, it is much more common to deal with `undefined` in the JS ecosystem, whether that is by omitting properties from objects, or explicitly assigning/returning `undefined` somewhere.
`T|null|undefined` types are ever rarer. Only for those it makes sense to test for both null and undefined.
By the way you can also have types like
type RemoteData<T> = {ready: false} | {ready: true, data: T}
in TypeScript, which is better than { ready: boolean, data?: T }
because you don't have to worry about "does `data` still make sense when it is non-ready?", the type clearly tells you that it doesn't (of course you can also have a different type where it would, the point is to accurately describe the structures you deal with). Then, if you do a check if (remote.ready) {
console.log(remote.data.length)
}
it knows that data exists inside that `if` block, so you can safely access it without `!` or `?`. Similarly, inside `if (!remote.ready) { }`, you cannot access it at all. It also won't let you pass an object with { ready: true }, but no data of the required type to `RemoteData<T>`.