The examples above or Either<A,A> could result from polymorpic functions that would return a set of types that the function is abstracting about, something like: pickRandom<S,T> : S, T -> S|T. With Either<S,T> you would get pickRandom<A,A> a1 a2 : Either<A,A> (requiring cleanup if you want the invariants I wrote about), with set theoretic types you'd get A. If you have pickRandom<A|B, B|C> x y you would get nested Either's or just A|B|C respectively.
Either is a Monad and so Haskell and others allow us to hide a bunch of complexity of reducing nestings by using abstractions and custom magic syntax (do notation) built for them - but the underlying complexity of the type and necessary mental model remains. Monad transformers become a necessity because you already needed the Monad magic for the cleanup, but you also have another Monad you care much more about then Either (like IO), see e.g the answer here https://stackoverflow.com/questions/67617871/reduce-nestedne... Note that this isn't talking about nested Either's, just the nested syntax for handling them without using it as a Monad and do notation, with actual nested Either's you'd need to do more cleanup.