I find it very hard to say how Tolkien would feel about these RPGs and fanfics. Because there are many RPGs and fanfictions out there that are not only well-written, but keep the facts and histories of Middle-Earth as they were written. Everything is left in the canon Tolkien established. Perhaps Tolkien would be flattered by these lovers of his work who took their time to keep the facts straight and write something for fun because they love Middle-Earth.
On the other hand you run into RPGs and fanfictions that completely bend things. They don't follow the books so much as they follow Peter Jackson's movies and the events added there (such as the Elves at Helm's Deep, Arwen on the verge of death, etc.) Many that follow those lines are nothing more than the writer expressing their crush for an actor in the film. Which is all fine and dandy, but would probably be frowned upon by Tolkien.
Having seen way more fanfics and RPGs that pretty much destroy the canon of Middle-Earth I'm going to have to say Tolkien would probably prefer only his son or others authorized editors should carry on his work.
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"Let us live so that when we come to die even the undertaker will be sorry." - Mark Twain
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