As best we understand the physics, there is not a hard limit. However, the expansion is not strong enough to pull apart objects that are bound together by gravity or other forces, so as long as structures exist at all they’ll be safe from the expansion of the Universe. That said, structures aren’t totally eternal as we understand the cosmos today, and it is likely that in the very, very, very far future the Universe will consist of isolated particles (primarily photons) so distant from one another that none of them can observe any other.
As for how – well, why *wouldn’t* it be able to? It *already* stretched by a factor of untold billions just after the Big Bang, so in a sense we’re already *in* a very, very stretched-out Universe.
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